Triethyl Phosphate → (rac)-Allyl 4-(4-cyano-2-nitrophenyl)-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimidine-5-carboxylate

HRID 336915

反応式

HRID 336915 の反応式
[C:1]([O:7][CH2:8][CH:9]=[CH2:10])(=[O:6])[CH2:2][C:3]([CH3:5])=O.[C:11]([C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[C:15]([N+:21]([O-:23])=[O:22])[CH:14]=1)#[N:12].[F:24][C:25]([F:37])([F:36])[C:26]1[CH:27]=[C:28]([NH:32][C:33]([NH2:35])=[O:34])[CH:29]=[CH:30][CH:31]=1.P(OCC)(OCC)(OCC)=O>C1COCC1.C(OCC)(=O)C>[C:11]([C:13]1[CH:20]=[CH:19][C:16]([CH:17]2[C:2]([C:1]([O:7][CH2:8][CH:9]=[CH2:10])=[O:6])=[C:3]([CH3:5])[N:32]([C:28]3[CH:29]=[CH:30][CH:31]=[C:26]([C:25]([F:36])([F:37])[F:24])[CH:27]=3)[C:33](=[O:34])[NH:35]2)=[C:15]([N+:21]([O-:23])=[O:22])[CH:14]=1)#[N:12]

参加物

7

反応物 4

HCID 6535Triethyl PhosphateHCID 25712(3-Trifluoromethylphenyl)ureaHCID 70701Allyl acetoacetateHCID 132385504-Formyl-3-nitrobenzonitrile

生成物 1

HCID 58133797(rac)-Allyl 4-(4-cyano-2-nitrophenyl)-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimidine-5-carboxylate

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

The reaction was carried out under argon. Allyl acetoacetate (5.94 g, 41.5 mmol; 1.0 eq.) was initially charged in THF (117 ml) at RT. Subsequently, 4-cyano-2-nitrobenzaldehyde (10.45 g, 41.5 mmol, purity 70%; 1.0 eq.), 1-[3-(trifluoromethyl)phenyl]urea (8.48 g, 41.5 mmol) and triethyl phosphate (17.7 g) were added. The mixture was stirred under reflux for 16 h. For work-up, initially ice-water was added, and the mixture was then taken up in ethyl acetate (400 ml). The organic phase was dried over solid sodium sulfate, filtered and concentrated under reduced pressure. The crude product was recrystallized from hot water/isopropanol (2:1, ˜400 ml). The solid obtained was triturated with diethyl ether (60 ml), once more filtered off with suction, washed with a little diethyl ether and dried under high vacuum. The title compound was obtained as a solid (16.63 g, 82% of theory).

後処理

  1. temperatureunder reflux for 16 h
  2. dry with materialThe organic phase was dried over solid sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was recrystallized from hot water/isopropanol (2:1, ˜400 ml)
  6. customThe solid obtained
  7. customwas triturated with diethyl ether (60 ml)
  8. filtrationonce more filtered off with suction
  9. washwashed with a little diethyl ether
  10. customdried under high vacuum

出典と根拠

ORDレコード
ord-e1a57b1af1fd4c488d0bc493661ed622
出典データセット
uspto-grants-2014_11
特許番号
US08889700B2

関連ノート

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