Water → N'-Methyl-2-(2-methyl-2-(phenylcarbonothioyl)hydrazinyl)-2-oxo-N'-(phenylcarbonothioyl)ethanesulfonohydrazide

HRID 1913511Notes

Reaction equation

HRID 1913511 reaction equation
[CH3:1][N:2]([C:4](=[S:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[NH2:3].Cl[S:13]([CH2:16][C:17](Cl)=[O:18])(=[O:15])=[O:14].O>C(Cl)Cl.N1C=CC=CC=1>[CH3:1][N:2]([C:4]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[S:11])[NH:3][S:13]([CH2:16][C:17]([NH:3][N:2]([CH3:1])[C:4]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[S:11])=[O:18])(=[O:15])=[O:14]

Participants

6

Reactant 3

HCID 962WaterHCID 77642(Chlorosulphonyl)acetyl chlorideHCID 12206211N-methylbenzothiohydrazide

Product 1

HCID 59267374N'-Methyl-2-(2-methyl-2-(phenylcarbonothioyl)hydrazinyl)-2-oxo-N'-(phenylcarbonothioyl)ethanesulfonohydrazideYield 36.6%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a 0° C. solution of N-methylbenzothiohydrazide (10 mmol) in DCM (20 mL) and pyridine (1 mL) was added 2-(chlorosulfonyl)acetyl chloride (5 mmol) dropwise. The mixture was kept at rt for 2 h before it was poured into water (20 ml). The organic layer was separated, dried and evaporated and the resulting residue was purified by column chromatography to give compound 68 as yellowish solids (0.8 g). 1H-NMR (CDCl3) δ 10.5 (m, 1H), 7.4 (m, 10H), 4.4 (m, 1H), 3.4-3.8 (m, 8H) ppm; ESMS calcd for C18H20N4O3S3:436.1; found: 437.2 (M+H+).

Workup

  1. customThe organic layer was separated
  2. customdried
  3. customevaporated
  4. customthe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-c7727f6a340942459d6d02d38eb31441
Source dataset
uspto-grants-2013_12
Patent number
US08609720B2

Reaction notes

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