3-(2-bromoethyl)thiophene → HCID 21520086, compound

HRID 1282785Notes

Reaction equation

HRID 1282785 reaction equation
[NH2:1][C:2]1[C:3]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:4]([SH:11])[CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].BrC[CH2:21][C:22]1[CH:26]=[CH:25][S:24][CH:23]=1>[OH-].[Na+]>[NH2:1][C:2]1[C:3]([O:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[C:4]([S:11][CH2:21][C:22]2[CH:26]=[CH:25][S:24][CH:23]=2)[CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 108779483-(2-bromoethyl)thiopheneHCID 215201075-Amino-3-mercapto-4-phenoxybenzoic acid

Product 1

HCID 21520086HCID 21520086, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 5-amino-3-mercapto-4-phenoxybenzoic acid (2.5 g) in 0.5 N sodium hydroxide (100 ml), a solution of 3-bromoethylthiophene (3.5 g in benzene (20 ml)) is added. The reacton mixture is stirred for 2 hours at room temperature. After extraction with additional benzene, the aqueous layer is acidified by addition of 4 N hydrochloric acid to precipitate 5-amino-4-phenoxy-3-(3-thienylmethylthio)benzoic acid. After collection by filtration, recrystallisation from aqueous ethanol and drying, the compound is obtained with a melting point of 153°-155°C.

Workup

  1. extractionAfter extraction with additional benzene
  2. additionthe aqueous layer is acidified by addition of 4 N hydrochloric acid
  3. customto precipitate 5-amino-4-phenoxy-3-(3-thienylmethylthio)benzoic acid
  4. customAfter collection
  5. filtrationby filtration, recrystallisation from aqueous ethanol
  6. customdrying
  7. customthe compound is obtained with a melting point of 153°-155°C.

Sources & evidence

ORD record
ord-00902f74a4864767a5a0e349bd04017f
Source dataset
uspto-grants-1976_08
Patent number
US03972886

Reaction notes

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