Dimethylformamide → 3-Chloro-4-hydroxybenzohydrazide

HRID 1166755Notes

Reaction equation

HRID 1166755 reaction equation
[ClH:1].CN(C)CCCN=C=NCC.C[N:14]([CH:16]=[O:17])C.[OH2:18].[NH2:19]N.ON1[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2N=N1>C(Cl)Cl>[Cl:1][C:26]1[CH:27]=[C:28]([CH:29]=[CH:30][C:25]=1[OH:18])[C:16]([NH:14][NH2:19])=[O:17]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24654Hydrazine hydrate (1:1)HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 109542683-Chloro-4-hydroxybenzohydrazide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The above resin (3.0 g) was suspended in CH2Cl2 (20 mL) and 1-hydroxybenzotriazole (0.6 g), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide, hydrochloride (0.9 g) and DMF (10 mL) were added. The mixture was shaken at room temperature for 45 minutes, hydrazine hydrate (300 μL) was added, and the mixture was shaken overnight at room temperature. The resin was successively washed with DMF (3×20 mL) and CH2Cl2 (3×20 mL) to afford resin bound 3-chloro-4-hydroxybenzoic acid hydrazide (Resin—[Building block 1]).

Workup

  1. stirringthe mixture was shaken overnight at room temperature
  2. washThe resin was successively washed with DMF (3×20 mL) and CH2Cl2 (3×20 mL)

Sources & evidence

ORD record
ord-3ccee833de9a452bb248eda4a4b74393
Source dataset
uspto-grants-2003_09
Patent number
US06613942B1

Reaction notes

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