Acetic Acid → 4-Chloro-thiobenzoic acid hydrazide

HRID 1694335Notes

Reaction equation

HRID 1694335 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([C:6](SCC(O)=O)=[S:7])=[CH:4][CH:3]=1.O.[NH2:16][NH2:17].C(O)(=O)C>[OH-].[Na+].C(Cl)Cl>[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([NH:16][NH2:17])=[S:7])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 593395S-[p-Chlorothiobenzoyl]thioglycolic acid

Product 1

HCID 124770754-Chloro-thiobenzoic acid hydrazide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a mixture of (4-chloro-thiobenzoylsulfanyl)-acetic acid (8.31 mmol) in 9 mL of NaOH (1N) is added hydrazine hydrate (36.7 mL). Glacial acetic acid (2.7 mL) is then added to the solution and the mixture is vigorously stirred. The reaction mixture is diluted with CH2Cl2 and the organic layer dried over MgSO4 to yield 4-chloro-thiobenzoic acid hydrazide: LC/MS (ES+) 186.9 (M+1)+.

Workup

  1. dry with materialthe organic layer dried over MgSO4

Sources & evidence

ORD record
ord-b99cc83e1a414d7ba05bd1fbf75332dc
Source dataset
uspto-grants-2012_04
Patent number
US08158662B2

Reaction notes

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