Dimethylformamide → 2-Cyano-N-cyclopropyl-N-[[(2-fluoro-4-iodophenyl)amino]carbonyl]acetamide

HRID 75656

반응식

HRID 75656 반응식
[CH:1]1([NH:4][C:5]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([I:14])=[CH:10][C:9]=2[F:15])=[O:6])[CH2:3][CH2:2]1.[C:16]([CH2:18][C:19](O)=[O:20])#[N:17].CN(C)C=O.CS(Cl)(=O)=O>O.C(O)(C)C.O>[C:16]([CH2:18][C:19]([N:4]([CH:1]1[CH2:2][CH2:3]1)[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([I:14])=[CH:10][C:9]=1[F:15])=[O:6])=[O:20])#[N:17]

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 9740Cyanoacetic acidHCID 31297Methanesulfonyl chlorideHCID 59717054N-Cyclopropyl-N'-(2-fluoro-4-iodophenyl)urea

생성물 1

HCID 597170362-Cyano-N-cyclopropyl-N-[[(2-fluoro-4-iodophenyl)amino]carbonyl]acetamide수율 95.1%

시약·촉매·용매 2

HCID 962Water용매HCID 21889133Propan-2-ol--water (1/1)용매

실험 절차

Under a nitrogen atmosphere, to 1-cyclopropyl-3-(2-fluoro-4-iodo-phenyl)-urea 48 (167 g) and cyanoacetic acid 73 (80.0 g), was added N,N-dimethylformamide (836 ml), and methanesulfonyl chloride (72.8 ml) was added dropwise with stirring at room temperature. The mixture was stirred at room temperature for 4 hrs. The reaction mixture was cooled with water, and water-isopropanol [2:1 (volume ratio), 1670 ml] was added dropwise. The mixture was stirred under water-cooling for 1 hr, and the precipitated crystals were collected by filtration and dried to give 1-(2-cyano-acetyl)-1-cyclopropyl-3-(2-fluoro-4-iodo-phenyl)-urea 74 (192 g).

후처리

  1. additionwas added dropwise
  2. stirringThe mixture was stirred at room temperature for 4 hrs
  3. additionwas added dropwise
  4. stirringThe mixture was stirred under water-
  5. temperaturecooling for 1 hr
  6. filtrationthe precipitated crystals were collected by filtration
  7. customdried

출처 및 근거

ORD 기록
ord-49db73fa634d49f2ad82112751b7b222
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835443B2

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