Chlorosulfonic acid → p-[2-[(5-Chloro-2-methoxybenzoyl)amino]ethyl]benzenesulfonic Acid

HRID 1658597Notes

Reaction equation

HRID 1658597 reaction equation
[CH2:1]([NH:9][C:10](=[O:20])[C:11]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=1[O:18][CH3:19])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[S:22]([OH:25])(=[O:24])=[O:23]>C(Cl)(Cl)Cl>[Cl:17][C:15]1[CH:14]=[CH:13][C:12]([O:18][CH3:19])=[C:11]([CH:16]=1)[C:10]([NH:9][CH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:22]([OH:25])(=[O:24])=[O:23])=[CH:5][CH:4]=1)=[O:20]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 1185755-chloro-2-methoxy-N-(2-phenylethyl)benzamide

Product 1

HCID 10044620p-[2-[(5-Chloro-2-methoxybenzoyl)amino]ethyl]benzenesulfonic Acid

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

N-phenethyl-5-chloro-2-methoxybenzamide (10 g.) dissolved in 25 ml. of chloroform was cooled to -10° and 19 g. of chlorosulfonic acid was added dropwise, maintaining the temperature at -10° to 0°. After the addition was complete the mixture was allowed to rise to room temperature and it was poured onto cracked ice. The crude sulfonic acid was filtered and 7.3 g. (57%) was obtained. A sample recrystallized for analysis from alcohol-acetonitrile melted at 188°-189°. Anal. Calcd. for C16H16ClNO5S: C, 51.94; H, 4.36; Cl, 9.58; N, 3.79; S, 8.67. Found: C, 50.10; H, 4.27; Cl, 9.93; N, 4.04; S, 8.84.

Workup

  1. temperaturemaintaining the temperature at -10° to 0°
  2. additionAfter the addition
  3. customto rise to room temperature
  4. additionit was poured
  5. filtrationThe crude sulfonic acid was filtered
  6. custom(57%) was obtained
  7. customA sample recrystallized for analysis from alcohol-acetonitrile melted at 188°-189°

Sources & evidence

ORD record
ord-bc8f02c5c844401397121a31c0651e41
Source dataset
uspto-grants-1976_06
Patent number
US03965173

Reaction notes

Loading…