In this paper, multicomponent reaction of amine, carbon disulfide and fluoronitrobenzene is reported for the synthesis of nitrophenyl methylcarbamodithioate derivatives. The method is based on the nucleophilic attack of the activated methylcarbamodithioate salt to fluoronitrobenzene. Several starting materials are tested and successfully produced the corresponding nitrophenyl methylcarbamodithioate. A possible mechanism for the reaction is suggested. K E Y W O R D S amine-CS 2 reaction, aromatic nucleophilic substitution, multicomponent reaction, nitrophenyl methylcarbamodithioate White solid; yield: 85%, mp = 210-215 C. IR (KBr): 3,053 (C-H aromatic ), 1,610 (C=S) cm −1 ; 1 H NMR (DMSO-d6, 500 MHz): δ = 3.87 (s, 3H, O-CH 3 ), 4.10 (m, 4H, N-CH 2-piperazine ), 4.51 (m, 4H, N-CH 2-piperazine ), 6.93 (d, J = 7.0 Hz, 1H, H 3 0 ), 7.03 (d, J = 7.5 Hz, 1H, H 6 0), 7.43 (t, J = 7.5 Hz, 1H, H 5 0 ), 7.57 (t, J = 7.0 Hz, 2H, H 4 0 ), 7.86 (d, J = 7.5 Hz, 2H, H 2,6 ), and 8.01 (d, J = 7.5 Hz, 2H, H 3,5 ) ppm; 13 C NMR (DMSO-d6, 125 MHz): δ = 50.2, 51.9, S C H E M E 2 Suggested mechanism for the synthesis of nitrophenyl methylcarbamodithioate derivatives White solid; yield: 75%, mp =203-205 C. IR (KBr): 3,062 (C-H aromatic ), 1,610 (C=S) cm −1 ; 1 H NMR (DMSO-d6, 500 MHz): δ = 4.09 (m, 4H, N-CH 2-piperazine ), 4.46 (m, 4H, N-CH 2-piperazine ), 6.84-6.99 (m, 5H, Ph), 7.43 (t, J = 7.5 Hz, 1H, H 5 ), 7.57 (t, J = 7.0 Hz, 2H, H 4 ), 7.85 (d, J = 7.5 Hz, 2H, H 6 ), and 8.01 (d, J = 7.5 Hz, 2H, H 3 ) ppm; 13 C NMR (DMSO-d6, 125 MHz): δ = 49. 9, 52.9, 115.7, 115.9, 118.4, 120.5, 128.9, 133.0, 133.4, 141.1, 141.5, 147.7, and 195.2 ppm; MS (70 eV): m/z = 359 (M+). 3.3.7 | 2-Nitrophenyl 4-(p-tolyl)piperazine-1-carbodithioate (4g) White solid; yield: 75%, mp =236-240 C. IR (KBr): 3,037 (C-H aromatic ), 1,608 (C=S) cm −1 ; 1 H NMR (DMSO-d6, 500 MHz): δ = 2.27 (s, 3H, CH 3 ), 4.07 (m, 4H, N-CH 2-piperazine ), 4.46 (m, 4H, N-CH 2-piperazine ), 6.81 (d, J = 8.0 Hz, 2H, H 3 0 ,5 0 ), 7.09 (d, J = 8.0 Hz, 2H, H 2 0 ,6 0 ), 7.43 (t, J = 7.5 Hz, 1H, H 5 ), 7.56 (t, J = 7.0 Hz, 2H, H 4 ), 7.85 (d, J = 7.5 Hz, 2H, H 6 ), and 8.01 (d, J = 7.5 Hz, 2H, H 3 ). ppm; 13 C NMR (DMSO-d6, 125 MHz): δ = 20.196.3 ppm; MS (70 eV): m/z = 373 (M+). 3.3.8 | 2-Nitrophenyl 4-benzylpiperazine-1-carbodithioate (4h)
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