Ethanol → Ethyl 3-benzylamino-5-sulphamyl-4-(m-trifluoromethylphenoxy)-benzoate

HRID 918683Notes

Reaction equation

HRID 918683 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:22](=[O:25])(=[O:24])[NH2:23])[C:10]=1[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=1)[C:5]([OH:7])=[O:6].[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[CH2:34](O)[CH3:35]>>[CH2:26]([NH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:22](=[O:24])(=[O:25])[NH2:23])[C:10]=1[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:19])([F:21])[F:20])[CH:13]=1)[C:5]([O:7][CH2:34][CH3:35])=[O:6])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 7498Benzyl BromideHCID 21312196Benzoic acid,3-amino-5-(aminosulfonyl)-4-[3-(trifluoromethyl)phenoxy]-

Product 1

HCID 21506121Ethyl 3-benzylamino-5-sulphamyl-4-(m-trifluoromethylphenoxy)-benzoate

Procedure

A mixture of 3-amino-5-sulphamyl-4-(m-trifluoromethylphenoxy)-benzoic acid (1.82 g), benzyl bromide (2 g), and anhydrous ethanol (15 ml) was refluxed for 7 hours. The soluton was cooled, and the precipitated ethyl 3-benzylamino-5-sulphamyl-4-(m-trifluoromethylphenoxy)-benzoate was collected by suction. After recrystallization from ethanol, the melting pont was 166°-168°C.

Workup

  1. temperaturewas refluxed for 7 hours
  2. temperatureThe soluton was cooled
  3. customthe precipitated ethyl 3-benzylamino-5-sulphamyl-4-(m-trifluoromethylphenoxy)-benzoate was collected by suction
  4. customAfter recrystallization from ethanol
  5. customwas 166°-168°C.

Sources & evidence

ORD record
ord-28492a745504426a8597d7e50e289c7d
Source dataset
uspto-grants-1976_07
Patent number
US03971819

Reaction notes

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