Phosgene → 1-chloro-N-(2-chloro-4-fluoro-5-isocyanatophenyl)methanesulfonamide

HRID 1107250

반응식

HRID 1107250 반응식
[C:1](Cl)(Cl)=[O:2].[NH2:5][C:6]1[C:7]([F:19])=[CH:8][C:9]([Cl:18])=[C:10]([NH:12][S:13]([CH2:16][Cl:17])(=[O:15])=[O:14])[CH:11]=1>C1(C)C=CC=CC=1>[Cl:17][CH2:16][S:13]([NH:12][C:10]1[CH:11]=[C:6]([N:5]=[C:1]=[O:2])[C:7]([F:19])=[CH:8][C:9]=1[Cl:18])(=[O:15])=[O:14]

참가 물질

4

반응물 2

HCID 6371PhosgeneHCID 11000212N-(5-amino-2-chloro4-fluorophenyl)-1-chloromethanesulfonamide

생성물 1

HCID 110774021-chloro-N-(2-chloro-4-fluoro-5-isocyanatophenyl)methanesulfonamide수율 95.5%

시약·촉매·용매 1

HCID 1140Toluene용매2회

실험 절차

To a stirred solution of phosgene (68 mmol) in 35 mL toluene was added the title compound of Step D (4.2 g, 15.4 mmol) in 80 mL toluene at 0° C. and the reaction was stirred at room temperature overnight. The temperature was then raised to 70° C. for 4 h. After cooling to room temperature, the reaction mixture was filtrated and the solvent was removed under reduced pressure. Drying of the white precipitate under reduced pressure yielded the title compound of Step E (4.4 g, 95%) melting at 101.5-102.5° C. 1H NMR (CDCl3) δ 7.5 (d, 1H), 7.3 (d, 1H), 7.0-6.9 (br s, 1H), 4.64.5 (s, 2H).

후처리

  1. temperatureThe temperature was then raised to 70° C. for 4 h
  2. temperatureAfter cooling to room temperature
  3. filtrationthe reaction mixture was filtrated
  4. customthe solvent was removed under reduced pressure
  5. customDrying of the white precipitate under reduced pressure

출처 및 근거

ORD 기록
ord-876da175843b498091fe36facd3e0ee5
출처 데이터셋
uspto-grants-2000_05
특허 번호
US06060432

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