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

HRID 1667678

Reaction equation

HRID 1667678 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]=[CH:28][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]=[CH:28][CH:27]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 866428042-(5-Dimethoxymethyl-2-nitro-phenylamino)-4-phenyl-thiazole-5-carboxylic acid ethyl ester

Product 1

HCID 866428052-(5-Formyl-2-nitro-phenylamino)-4-phenyl-thiazole-5-carboxylic acid ethyl esterYield 100.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 0.089 g (0.2 mmole) of 2-(5-dimethoxymethyl-2-nitro-phenylamino)-4-phenyl-thiazole-5-carboxylic acid ethyl ester (VI.1a), 2 mL of actonitrile and 0.5 mL of 1 M hydrochloric acid was stirred at 60 degrees for 30 minutes. The mixture was concentrated under reduced pressure. The residue was diluted with 5 mL of saturated sodium bicarbonate and extracted twice with 20 mL of dichloromethane. The combined organic layers were washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give 0.080 g of 2-(5-formyl-2-nitro-phenylamino)-4-phenyl-thiazole-5-carboxylic acid ethyl ester (VI.1b) as an orange oil. The crude was carried to the next step reaction without further purification.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionThe residue was diluted with 5 mL of saturated sodium bicarbonate
  3. extractionextracted twice with 20 mL of dichloromethane
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-db49e020fbc747b282916d2477dc0549
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Linked notes

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