2-(Ethoxymethylene)propanedinitrile → 5-amino-1-(2-fluoro-4-methanesulfonyl-phenyl)-1H-pyrazole-4-carbonitrile

HRID 31379

반응식

HRID 31379 반응식
[F:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[NH:12][NH2:13].C(O[CH:17]=[C:18]([C:21]#[N:22])[C:19]#[N:20])C>CO>[NH2:22][C:21]1[N:12]([C:3]2[CH:4]=[CH:5][C:6]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:7][C:2]=2[F:1])[N:13]=[CH:17][C:18]=1[C:19]#[N:20]

참가 물질

4

반응물 2

HCID 671522-(Ethoxymethylene)propanedinitrileHCID 2782739[2-Fluoro-4-(methylsulfonyl)phenyl]hydrazine

생성물 1

HCID 218975935-amino-1-(2-fluoro-4-methanesulfonyl-phenyl)-1H-pyrazole-4-carbonitrile

시약·촉매·용매 1

HCID 887Methanol용매2회

반응 조건

온도
-6 °C

실험 절차

To a stirred suspension of 2-fluoro-4-methylsulfonylphenyl hydrazine (1) (4.0336 Kg; 1 eq) (commercially available from, e.g., Peakdale Molecular, Ltd.) in methanol (12.7723 Kg) was added a suspension of ethoxymethylene malononitrile (2.6564 Kg, 1.101 equivalents) in methanol (11.212 Kg) at a rate sufficiently slow to maintain the reaction mixture at −10° to 0° C. with reactor jacket cooling. After the addition had been completed, the reaction mixture was stirred for 1 hour at −6° C. and then heated to reflux for 5 hours, at which time the reaction mixture gave a pyrazole (3): hydrazine (1) HPLC peak area ratio of 105:1. Solvent (20.5153 Kg) was then distilled off the reaction mixture at atmospheric pressure, leaving a residue having less than 20% of the original volume. The resulting mixture was used directly in the next step.

후처리

  1. temperatureto maintain the reaction mixture at −10° to 0° C. with reactor jacket
  2. temperaturecooling
  3. additionAfter the addition
  4. temperatureheated
  5. temperatureto reflux for 5 hours, at which time the reaction mixture

출처 및 근거

ORD 기록
ord-2cf28deae1a344dd9efb094b5ca7a968
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425630B2

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