2-Iodobutane → 5-Amino-3-sec-butylthio-4-phenoxybenzoic acid

HRID 1605514Notes

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].[CH:19](I)([CH2:21][CH3:22])[CH3:20]>C(=O)([O-])O.[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][CH:19]([CH2:21][CH3:22])[CH3:20])[CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]

Participants

Conditions

Temperature: 55 °C

Procedure

A mixture of 5-amino-3-mercapto-4-phenoxybenzoic acid (2.6 g), sodium hydrogen carbonate (2 g), saturated sodium hydrogen carbonate (100 ml), and sec.-butyl iodide (2.2 g) is stirred for 6 hours at 55° C. After cooling, 5-amino-3-sec.-butylthio-4-phenoxybenzoic acid is precipitated by addition of hydrochloric acid until pH 2.5. After collection, recrystallization from aqueous ethanol, and drying in vacuo at 80° C, the compound is obtained with a melting point of 157°-159° C.

Workup

temperatureAfter cooling
custom5-amino-3-sec.-butylthio-4-phenoxybenzoic acid is precipitated by addition of hydrochloric acid until pH 2.5
customAfter collection, recrystallization from aqueous ethanol
customdrying in vacuo at 80° C
customthe compound is obtained with a melting point of 157°-159° C.

Sources & evidence

ORD record: ord-d3d4682a67e54a52bbe132eaa35ddd09
Source dataset: uspto-grants-1976_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03950376

Reaction notes

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