1-Bromopentane → 5-Amino-3-n-pentylthio-4-phenoxybenzoic acid

HRID 1605515Notes

Reaction equation

HRID 1605515 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].[CH2:19](Br)[CH2:20][CH2:21][CH2:22][CH3:23].[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][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]

Participants

4

Reactant 3

HCID 80571-BromopentaneHCID 14798Sodium HydroxideHCID 215201075-Amino-3-mercapto-4-phenoxybenzoic acid

Product 1

HCID 542166355-Amino-3-n-pentylthio-4-phenoxybenzoic acid

Procedure

A mixture of 5-amino-3-mercapto-4-phenoxybenzoic acid (5.2 g), n-pentyl bromide (5 ml), and 0.5 N sodium hydroxide is stirred at room temperature for 5 days. 5-Amino-3-n-pentylthio-4-phenoxybenzoic acid is precipitated by addition of 4 N hydrochloric acid (30 ml). After collection by filtration, recrystallisation from cyclohexane and drying, the compound is obtained from a melting point of 98° C.

Workup

  1. custom5-Amino-3-n-pentylthio-4-phenoxybenzoic acid is precipitated by addition of 4 N hydrochloric acid (30 ml)
  2. customAfter collection
  3. filtrationby filtration, recrystallisation from cyclohexane
  4. customdrying
  5. customthe compound is obtained from a melting point of 98° C.

Sources & evidence

ORD record
ord-94f733ea319a42b09f7517bb8bad78cb
Source dataset
uspto-grants-1976_04
Patent number
US03950376

Reaction notes

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