Dichloromethane → 4-{3-[3-[2-(1-Hydroxycyclohexyl)ethyl]-4-oxo-2-thiazolidinyl]propyl}benzoic Acid Hydrazide

HRID 28222Notes

Reaction equation

HRID 28222 reaction equation
[OH:1][C:2]1([CH2:8][CH2:9][N:10]2[C:14](=[O:15])[CH2:13][S:12][CH:11]2[CH2:16][CH2:17][CH2:18][C:19]2[CH:28]=[CH:27][C:22]([C:23](OC)=[O:24])=[CH:21][CH:20]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.O.[NH2:30][NH2:31].ClCCl>CO>[OH:1][C:2]1([CH2:8][CH2:9][N:10]2[C:14](=[O:15])[CH2:13][S:12][CH:11]2[CH2:16][CH2:17][CH2:18][C:19]2[CH:28]=[CH:27][C:22]([C:23]([NH:30][NH2:31])=[O:24])=[CH:21][CH:20]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 24654Hydrazine hydrate (1:1)HCID 13174084Methyl 4-{3-[3-[2-(1-Hydroxycyclohexyl)ethyl]-4-oxo-2-thiazolidinyl]propyl}benzoate

Product 1

HCID 867372444-{3-[3-[2-(1-Hydroxycyclohexyl)ethyl]-4-oxo-2-thiazolidinyl]propyl}benzoic Acid Hydrazide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 4-{3-[3-[2-(1-hydroxycyclohexyl)ethyl]-4-oxo-2-thiazolidinyl]propyl}benzoate (4.1 g., 0.01 mole) and hydrazine hydrate (2.5 g., 0.05 mole) in methanol (25 ml.) is stored at 25° C. for 48 hours. The solvent is then removed by distillation at reduced pressure. The residue is treated with water and enough 2 N hydrochloric acid to give a neutral mixture. The title compound is isolated by extraction into dichloromethane and subsequent drying and evaporation of the extract.

Workup

  1. customThe solvent is then removed by distillation at reduced pressure
  2. additionThe residue is treated with water and enough 2 N hydrochloric acid
  3. customto give a neutral mixture

Sources & evidence

ORD record
ord-cc169145f6f0448d8fe67ce6fc03b3a7
Source dataset
uspto-grants-1980_09
Patent number
US04225609

Reaction notes

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