2,5-Dimethoxytetrahydrofuran → 4-Phenoxy-3-(1H-pyrrol-1-yl)-5-sulfamoylbenzoic acid

HRID 47095

Reaction equation

HRID 47095 reaction equation
[S:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([NH2:21])[C:13]=1[O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:8]([OH:10])=[O:9])(=[O:4])(=[O:3])[NH2:2].CO[CH:24]1[CH2:28][CH2:27][CH:26](OC)O1>C(O)(=O)C>[S:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([N:21]2[CH:24]=[CH:28][CH:27]=[CH:26]2)[C:13]=1[O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:8]([OH:10])=[O:9])(=[O:3])(=[O:4])[NH2:2]

Participants

4

Reactant 2

HCID 790982,5-DimethoxytetrahydrofuranHCID 1199273-Amino-4-phenoxy-5-sulfamoylbenzoic acid

Product 1

HCID 128811314-Phenoxy-3-(1H-pyrrol-1-yl)-5-sulfamoylbenzoic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 3-sulphamoyl-4-phenoxy-5-amino-benzoic acid (3.08 g=10 mmols); P. W. Feit, J. Med. Chem. 14,432 (1971), 2,5-dimethoxy-tetrahydrofurane (1.32 g=10 mmols) and 5 ml of glacial acetic acid is refluxed for 15 minutes in an oil bath and evaporated to dryness in vacuo and the residue is recrystallised from ethyl acetate; the compound melts at 209°-210° C.

Workup

  1. customevaporated to dryness in vacuo
  2. customthe residue is recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-95cb7f59645a4f7aadd008677146636c
Source dataset
uspto-grants-1979_11
Patent number
US04176190

Linked notes

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