Hydrochloric Acid → N-[4-chloro-5-[[(chloromethyl)sulfonyl]amino]-2-fluorophenyl]acetamide
Reaction equation
[NH2:1][C:2]1[C:3]([Cl:13])=[CH:4][C:5]([F:12])=[C:6]([NH:8][C:9](=[O:11])[CH3:10])[CH:7]=1.N1C=CC=CC=1.[Cl:20][CH2:21][S:22](Cl)(=[O:24])=[O:23].Cl>O.C(OCC)(=O)C>[Cl:13][C:3]1[C:2]([NH:1][S:22]([CH2:21][Cl:20])(=[O:24])=[O:23])=[CH:7][C:6]([NH:8][C:9](=[O:11])[CH3:10])=[C:5]([F:12])[CH:4]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 20 °C
Procedure
1000 g of crude N-(5-amino-4-chloro-2-fluorophenyl)acetamide (4.93 mol) which still contained 1 L of ethyl acetate was dissolved in 3900 g (49.3 mol) of pyridine at 20° C. To the yellow solution was added 845 g (5.42 mol) of chloromethanesulfonyl chloride at 20-30° C. over 1-2 hours. The solution was allowed to stir for 1 additional hour. 2300 g of pyridine were distilled off under reduced pressure at 40° C. To the remaining reaction mixture were added 5.3 L of water and 1.7 L of concentrated HCl (pH 3) whereupon the product precipitated. The slurry was cooled to 20° C. and filtered off. The filter cake was washed twice with 1300 mL of water. The product was dried in vacuo at 70° C. to yield 1500 g (92% purity) of the title compound as a solid melting at 210° C.
Workup
- distillation2300 g of pyridine were distilled off under reduced pressure at 40° C
- customTo the remaining reaction mixture
- customprecipitated
- filtrationfiltered off
- washThe filter cake was washed twice with 1300 mL of water
- customThe product was dried in vacuo at 70° C.
Sources & evidence
- ORD record
- ord-ebe52c9d789b40cea434a8fc394874d6
- Source dataset
- uspto-grants-2002_05
- Patent number
- US06384234B1
Reaction notes
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