Hydrochloric Acid → 5-Methylthio-6-trifluoromethyl-1-(3-carboxy Phenyl Carbamoyl)indoline

HRID 989179Notes

Reaction equation

HRID 989179 reaction equation
[CH3:1][S:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[C:12]([F:15])([F:14])[F:13])[N:8]([C:16](=[O:29])[NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([O:26]CC)=[O:25])[CH:19]=1)[CH2:7][CH2:6]2.[OH-].[Na+].Cl>C(O)C>[CH3:1][S:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[C:12]([F:13])([F:14])[F:15])[N:8]([C:16](=[O:29])[NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([OH:26])=[O:25])[CH:19]=1)[CH2:7][CH2:6]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 180051605-Methylthio-6-trifluoromethyl-1-(3-ethoxycarbonylphenyl carbamoyl)-indoline

Product 1

HCID 180051075-Methylthio-6-trifluoromethyl-1-(3-carboxy Phenyl Carbamoyl)indolineYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 5-methylthio-6-trifluoromethyl-1-(3-ethoxy carbonyl phenyl carbamoyl) indoline (3 g, 7.1 mmol) in ethanol (30 ml) was added aqueous sodium hydroxide solution (5M) (7.1 ml, 35.5 mmol) and heated gently for 2 hours. It was then allowed to cool and acidified with aqueous hydrochloric acid (5M) forming a white precipitate which was filtered and dried to yield the product as a white solid (2.324 g, 83%), m.p.>200° C.

Workup

  1. temperatureheated gently for 2 hours
  2. temperatureto cool
  3. customforming a white precipitate which
  4. filtrationwas filtered
  5. customdried

Sources & evidence

ORD record
ord-bc42527dc65c419c8ccc9a164d678016
Source dataset
uspto-grants-2003_10
Patent number
US06638953B2

Reaction notes

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