Hydrochloric Acid → 2-(2-Amino-5-benzyloxy-phenylamino)-4-(3-chloro-phenyl)-thiazole-5-carboxylic acid ethyl ester

HRID 1667729Notes

Reaction equation

HRID 1667729 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([NH:11][C:12]2[CH:17]=[C:16]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:15]=[CH:14][C:13]=2[N+:26]([O-])=O)=[N:8][C:7]=1[C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[CH:30]=1)=[O:5])[CH3:2].Cl>[Zn].O1CCCC1>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([NH:11][C:12]2[CH:17]=[C:16]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:15]=[CH:14][C:13]=2[NH2:26])=[N:8][C:7]=1[C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[CH:30]=1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 866428302-(5-Benzyloxy-2-nitro-phenylamino)-4-(3-chloro-phenyl)-thiazole-5-carboxylic acid ethyl ester

Product 1

HCID 866428312-(2-Amino-5-benzyloxy-phenylamino)-4-(3-chloro-phenyl)-thiazole-5-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 5.09 g (10 mmole) of 2-(5-benzyloxy-2-nitro-phenylamino)-4-(3-chloro-phenyl)-thiazole-5-carboxylic acid ethyl ester (VI.25), 100 mL of tetrahydrofuran and 20 mL of 1M hydrochloric acid, was added portionwise, 10 g of zinc powder. The mixture was stirred at ambient temperature for 2 hours. The solid was removed by filtration, the filtrate was concentrated under reduced pressure and 200 mL of water was added to the residue. The pH was adjusted to 9 by addition of 15% sodium hydroxide. The precipitate was collected by filtration to give crude 2-(2-amino-5-benzyloxy-phenylamino)-4-(3-chloro-phenyl)-thiazole-5-carboxylic acid ethyl ester (VII.25). This material was carried through to next reaction without further purification.

Workup

  1. additionwas added portionwise
  2. customThe solid was removed by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure and 200 mL of water
  4. additionwas added to the residue
  5. additionThe pH was adjusted to 9 by addition of 15% sodium hydroxide
  6. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-10bcf7b135a24d4c98cb9f146ead0400
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Reaction notes

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