Ethanol → Ethyl 3-benzylamino-5-methylsulphamyl-4-phenoxy-benzoate

HRID 918692Notes

Reaction equation

HRID 918692 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:18](=[O:22])(=[O:21])[NH:19][CH3:20])[C:10]=1[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:5]([OH:7])=[O:6].[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[CH2:31](O)[CH3:32]>>[CH2:23]([NH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:18](=[O:22])(=[O:21])[NH:19][CH3:20])[C:10]=1[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:5]([O:7][CH2:31][CH3:32])=[O:6])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 7498Benzyl Bromide2×HCID 215060143-Amino-5-methylsulphamyl-4-phenoxy-benzoic acid

Product 1

HCID 21506047Ethyl 3-benzylamino-5-methylsulphamyl-4-phenoxy-benzoate

Procedure

A mixture of 3-amino-5-methylsulphamyl-4-phenoxy-benzoic acid (1 g), benzyl bromide (1.25 g), and dry ethanol (15 ml) was refluxed for 9 hours. After 3 hours and after 6 hours more benzyl bromide (0.6 g) was added. After cooling, the precipitated ethyl 3-benzylamino-5-methylsulphamyl-4-phenoxy-benzoate was collected by suction, recrystallized from ethanol, and dried in vacuo. The melting point of the compound was 162.5°C.

Workup

  1. temperaturewas refluxed for 9 hours
  2. temperatureAfter cooling
  3. customthe precipitated ethyl 3-benzylamino-5-methylsulphamyl-4-phenoxy-benzoate was collected by suction
  4. customrecrystallized from ethanol
  5. customdried in vacuo
  6. customwas 162.5°C.

Sources & evidence

ORD record
ord-448c90499bad40af8244bd3533441347
Source dataset
uspto-grants-1976_07
Patent number
US03971819

Reaction notes

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