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Hydrochloric Acid → N-[4-chloro-5-[[(chloromethyl)sulfonyl]amino]-2-fluorophenyl]acetamide

HRID 1934830
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HRID 1934830 반응식
[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]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 77054(Chloromethyl)sulfonyl chlorideHCID 11769584N-(5-amino-4-chloro-2-fluorophenyl)acetamide

생성물 1

HCID 10870764N-[4-chloro-5-[[(chloromethyl)sulfonyl]amino]-2-fluorophenyl]acetamide

시약·촉매·용매 2

HCID 962Water
용매
HCID 8857Ethyl Acetate용매

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온도
20 °C

실험 절차

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.

후처리

  1. distillation2300 g of pyridine were distilled off under reduced pressure at 40° C
  2. customTo the remaining reaction mixture
  3. customprecipitated
  4. filtrationfiltered off
  5. washThe filter cake was washed twice with 1300 mL of water
  6. customThe product was dried in vacuo at 70° C.

출처 및 근거

ORD 기록
ord-ebe52c9d789b40cea434a8fc394874d6
출처 데이터셋
uspto-grants-2002_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06384234B1

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