(Trifluoromethyl)benzene → Phenylsulfamoyl chloride
Reaction equation
[Na+].[C:2]1([NH:8][S:9](=[O:12])(=O)[O-:10])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:14].C1(C(F)(F)F)C=CC=CC=1>>[C:2]1([NH:8][S:9]([Cl:14])(=[O:12])=[O:10])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
Conditions
- Temperature
- 70 °C
Procedure
Phenyl sulfamic acid sodium salt (1.0 g), prepared by the method of Audrieth L. F et al, J. Org. Chem. 1944, 9, 89-101, and PCl5, 1.16 g were combined in the absence of solvent. After the exotherm subsided the contents were heated for a further 16 h at 70° C. Benzotrifluoride (5 mL) was added and the contents heated for a further 2 h, cooled, filtered and concentrated to give 182 mg of phenylsulfamoyl chloride. Compound 5 (Y═H) as its hydrochloride salt (20 mg, 0.085 mmol) was dissolved in 1 mL of dry CH2Cl2, and phenylsulfamoyl chloride (34 mg) in 0.5 mL of CH2Cl2 was added in portions followed by triethylamine (50 μL, 36 mg) in 0.5 mL of CH2Cl2. After stirring at ambient temperature for 16 h the reaction was quenched with saturated NaHCO3, separated, washed with water and brine, dried and purified by flash column chromatography (2% EtOAc in CH2Cl2) to give 20 mg of the title compound. LC-MS RT=3.56 min. (M−H)− 395.
Workup
- temperaturethe contents heated for a further 2 h
- temperaturecooled
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-e3c3a52291104b279755725f2e417049
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08324203B2
Reaction notes
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