N-Acetylsulfanilyl chloride → HCID 18552221, compound
Reaction equation
[C:1]([NH:4][C:5]1[CH:14]=[CH:13][C:8]([S:9](Cl)(=[O:11])=[O:10])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].Br.[Br:16][CH2:17][CH2:18][CH2:19][NH2:20].C(=O)([O-])O.[Na+]>CC(C)=O.O>[C:1]([NH:4][C:5]1[CH:14]=[CH:13][C:8]([S:9]([NH:20][CH2:19][CH2:18][CH2:17][Br:16])(=[O:11])=[O:10])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 2.5 °C
Procedure
To a stirred solution of N-acetylsulfanilyl chloride (57.15 g, 0.244 mol) in acetone (500 mL) and H2O (187.5 mL) at 0° C. was added 3-bromopropylamine hydrobromide (25.0 g, 0.114 mol). When a clear solution was obtained, a solution of sodium hydrogencarbonate (44.15 g, 0.526 mol) in H2O (550 mL) was added dropwise, maintaining the internal temperature at 0-5° C. When the addition was completed, the reaction mixture was heated at 50° C. for 5 h, then cooled to room temperature and poured into ice H2O with stirring. After stirring at 5° C. for 4 h, the suspension was filtered and the filter cake was washed with H2O and dried in vacuo to give 34.6 g (90%). An additional reaction was performed to give an additional 63.7 g of similar material.
Workup
- customWhen a clear solution was obtained
- additionWhen the addition
- temperaturethe reaction mixture was heated at 50° C. for 5 h
- temperaturecooled to room temperature
- stirringAfter stirring at 5° C. for 4 h
- filtrationthe suspension was filtered
- washthe filter cake was washed with H2O
- customdried in vacuo
- customto give 34.6 g (90%)
- customAn additional reaction
Sources & evidence
- ORD record
- ord-d423130fef2d42b095e0a06a772435ff
- Source dataset
- uspto-grants-2003_04
- Patent number
- US06544499B1
Reaction notes
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