Hydrochloric Acid → 4-(3-Chloro-phenyl)-2-(5-formyl-2-nitro-phenylamino)-thiazole-5-carboxylic acid ethyl ester

HRID 1667760Notes

Reaction equation

HRID 1667760 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([NH:11][C:12]2[CH:17]=[C:16]([CH:18](OC)[O:19]C)[CH:15]=[CH:14][C:13]=2[N+:23]([O-:25])=[O:24])=[N:8][C:7]=1[C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[CH:27]=1)=[O:5])[CH3:2].Cl>C(#N)C>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([NH:11][C:12]2[CH:17]=[C:16]([CH:18]=[O:19])[CH:15]=[CH:14][C:13]=2[N+:23]([O-:25])=[O:24])=[N:8][C:7]=1[C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[CH:27]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 866428354-(3-Chloro-phenyl)-2-(5-dimethoxymethyl-2-nitro-phenylamino)-thiazole-5-carboxylic acid ethyl ester

Product 1

HCID 866428364-(3-Chloro-phenyl)-2-(5-formyl-2-nitro-phenylamino)-thiazole-5-carboxylic acid ethyl esterYield 978.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3.4 g (0.71 mmole) of 4-(3-chloro-phenyl)-2-(5-dimethoxymethyl-2-nitro-phenylamino)-thiazole-5-carboxylic acid ethyl ester (VI.41a), 80 mL of acetonitrile and 20 mL of 1M hydrochloric acid was heated 60 degrees for 30 minutes. The mixture was concentrated under reduced pressure, 200 mL of water was added and the pH was adjusted to 9 by the addition of 15% sodium hydroxide solution. The precipitate was collected by filtration to give 3.0 g of 4-(3-chloro-phenyl)-2-(5-formyl-2-nitro-phenylamino)-thiazole-5-carboxylic acid ethyl ester (VI.41b) as a white solid.

Workup

  1. temperaturewas heated 60 degrees for 30 minutes
  2. concentrationThe mixture was concentrated under reduced pressure, 200 mL of water
  3. additionwas added
  4. additionthe pH was adjusted to 9 by the addition of 15% sodium hydroxide solution
  5. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-868149746958472ba167f992e660b573
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Reaction notes

Loading…