Acetic Anhydride → 2-(4-(4-(Butyl(1-methylhexyl)amino)phenyl)-3-cyano-1,5-dihydro-5-oxo-2H-pyrrol-2-ylidene)propanedinitrile

HRID 478113

반응식

HRID 478113 반응식
[Na][Na].[C:3]([C:5]1[C:9](=[C:10]([C:13]#[N:14])[C:11]#[N:12])[NH:8][C:7](=[O:15])[C:6]=1O)#[N:4].[CH2:17]([N:21]([CH:28]([CH3:34])[CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:18][CH2:19][CH3:20].C(OC(=O)C)(=O)C.P(Cl)(Cl)(Cl)=O>CC(C)=O.O.CN(C)C=O>[CH2:17]([N:21]([C:22]1[CH:23]=[CH:24][C:25]([C:6]2[C:7](=[O:15])[NH:8][C:9](=[C:10]([C:13]#[N:14])[C:11]#[N:12])[C:5]=2[C:3]#[N:4])=[CH:26][CH:27]=1)[CH:28]([CH3:34])[CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:18][CH2:19][CH3:20]

참가 물질

9

반응물 5

HCID 7918Acetic AnhydrideHCID 24813Phosphorus oxychlorideHCID 141233DisodiumHCID 18000381N-Butyl-N-(heptan-2-YL)anilineHCID 180003824-Cyano-5-dicyanomethylidene-3-hydroxy-2-oxo-2,5-dihydropyrrole

생성물 1

HCID 180003802-(4-(4-(Butyl(1-methylhexyl)amino)phenyl)-3-cyano-1,5-dihydro-5-oxo-2H-pyrrol-2-ylidene)propanedinitrile수율 65%

시약·촉매·용매 3

HCID 180Acetone용매HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

A stirred mixture of the disodium salt of 4-cyano-5-dicyanomethylidene-3-hydroxy-2-oxo-2,5-dihydropyrrole (23 parts) and dry N,N-dimethylformamide (180 parts) was cooled to −5° C. to −10° C. and N-n-butyl-N-(1-methylhexyl)aniline containing -acetic anhydride (27%, 37 parts) was added followed by the dropwise addition of phosphorous oxychloride (26 parts) whilst maintaining the temperature at less than −5° C. The mixture was allowed to warm to room temperature and stirred for 20 hours. The reaction mixture was poured into a stirred mixture of ice and water (400 parts) and acetone (400 parts) was added before filtering off a solid. The solid was washed repeatedly with warm water (40° C.) and then dried at 50° C. to yield 3-(4-(N-butyl-N-(1-methylhexyl)amino)phenyl)-4-cyano-5-dicyanomethylidene-2-oxo-2,5-dihydropyrrole (26.8 parts, 65%). A small sample of this material was slurried in boiling methanol, collected by filtration, washed with methanol and dried at 50° C. to give 3-(4-(N-n-butyl-N-(1-methylhexyl)amino)phenyl)-4-cyano-5-dicyanomethylidene-2-oxo-2,5-dihydropyrrole m.p. 180° C.; λmax (CH2Cl2) 662 nm (εmax 60231); M/Z (EI) 415 (M+, 20%), 400 (15), 372 (12), 344 (100), 288 (33) and 272 (25).

후처리

  1. temperaturewas cooled to −5° C. to −10° C.
  2. temperaturewhilst maintaining the temperature at less than −5° C
  3. additionwas added
  4. filtrationbefore filtering off a solid
  5. washThe solid was washed repeatedly with warm water (40° C.)
  6. customdried at 50° C.

출처 및 근거

ORD 기록
ord-aa32393232fd4fdaad3d24625c96a61a
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06641620B1

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