Carbon Disulfide → N-(4-Aminophenyl)hydrazinecarbothioamide

HRID 2070218Notes

Reaction equation

HRID 2070218 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][C:4]([NH2:7])=[CH:3][CH:2]=1.[C:9](=[S:11])=S.[OH-].[Na+].ClCC([O-])=O.[Na+].[NH2:20][NH2:21]>>[NH2:7][C:4]1[CH:5]=[CH:6][C:1]([NH:8][C:9](=[S:11])[NH:20][NH2:21])=[CH:2][CH:3]=1

Participants

6

Reactant 5

HCID 6348Carbon DisulfideHCID 7814P-PhenylenediamineHCID 9321HydrazineHCID 14798Sodium HydroxideHCID 23665759Sodium chloroacetate

Product 1

HCID 15812111N-(4-Aminophenyl)hydrazinecarbothioamideYield 38%

Procedure

As per general procedure (9) except with benzene-1,4-diamine (2.16 g, 20.00 mmol), CS2 (1.20 mL, 20.00 mmol), NaOH (0.80 g, 20.00 mmol), sodium chloroacetate (2.33 g, 20.00 mmol) and NH2NH2 (5.60 mL, 0.18 mol). The product was isolated as a cream solid (1.37 g, 38%). 1H NMR: δ 4.65 (2H, s, PhNH2); 4.95 (2H, s, NHNH2); 6.49 (2H, d, J 8.65, 3-ArH); 7.08 (2H, d, J 8.30, 2-ArH); 8.80 (1H, s, NH); 9.25 (1H, s, NHNH2).

Sources & evidence

ORD record
ord-d3ef9f06a60c4ef78f9d881b34ea8c0f
Source dataset
uspto-grants-2012_10
Patent number
US08299285B2

Reaction notes

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