Ethanol → Ethyl 3-benzylamino-5-sulphamyl-4-(beta,beta, beta-trifluoroethoxy)-benzoate

HRID 918686Notes

Reaction equation

HRID 918686 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:17](=[O:20])(=[O:19])[NH2:18])[C:10]=1[O:11][CH2:12][C:13]([F:16])([F:15])[F:14])[C:5]([OH:7])=[O:6].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[CH2:29](O)[CH3:30]>>[CH2:21]([NH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:17](=[O:19])(=[O:20])[NH2:18])[C:10]=1[O:11][CH2:12][C:13]([F:14])([F:16])[F:15])[C:5]([O:7][CH2:29][CH3:30])=[O:6])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 7498Benzyl BromideHCID 215060013-Amino-5-sulphamyl-4-(beta,beta,beta-trifluoroethoxy)-benzoic acid

Product 1

HCID 21505983Ethyl 3-benzylamino-5-sulphamyl-4-(beta,beta, beta-trifluoroethoxy)-benzoate

Procedure

A mixture of 3-amino-5-sulphamyl-4-(β, β, β-trifluoroethoxy)-benzoic acid (0.6 g), benzyl bromide (1.2 g), and dry ethanol (8 ml) was refluxed for 5 hours. After cooling, the precipitated ethyl 3-benzylamino-5-sulphamyl-4-(β, β, β-trifluoroethoxy)-benzoate was collected by suction and recrystallized from dry ethanol. After drying, the compound had a melting point of 163-165°C.

Workup

  1. temperaturewas refluxed for 5 hours
  2. temperatureAfter cooling
  3. customthe precipitated ethyl 3-benzylamino-5-sulphamyl-4-(β, β, β-trifluoroethoxy)-benzoate was collected by suction
  4. customrecrystallized from dry ethanol
  5. customAfter drying

Sources & evidence

ORD record
ord-a62ca07907e445099d9446cee06bad31
Source dataset
uspto-grants-1976_07
Patent number
US03971819

Reaction notes

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