Dicyclohexylcarbodiimide → 3-pentanone O-{2-chloro-5-[3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyrimidinyl]-4-fluorobenzoyl}oxime

HRID 2248556

반응식

HRID 2248556 반응식
[CH3:1][CH2:2][C:3](=[N:6][OH:7])[CH2:4][CH3:5].[Cl:8][C:9]1[CH:17]=[C:16]([F:18])[C:15]([N:19]2[C:24](=[O:25])[CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[N:21]([CH3:30])[C:20]2=[O:31])=[CH:14][C:10]=1[C:11](O)=[O:12].C1(N=C=NC2CCCCC2)CCCCC1.N1(C2C=CN=CC=2)CCCC1>C(OCC)C>[Cl:8][C:9]1[CH:17]=[C:16]([F:18])[C:15]([N:19]2[C:24](=[O:25])[CH:23]=[C:22]([C:26]([F:27])([F:28])[F:29])[N:21]([CH3:30])[C:20]2=[O:31])=[CH:14][C:10]=1[C:11]([O:7][N:6]=[C:3]([CH2:4][CH3:5])[CH2:2][CH3:1])=[O:12]

참가 물질

6

반응물 4

HCID 10868DicyclohexylcarbodiimideHCID 755674-PyrrolidinopyridineHCID 28017453-Pentanone oximeHCID 120567892-Chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]benzoic acid

생성물 1

HCID 199942333-pentanone O-{2-chloro-5-[3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyrimidinyl]-4-fluorobenzoyl}oxime

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

0.9 g of 3-pentanone oxime is added at room temperature to a suspension of 3.0 g of 2-chloro-5-[3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyrimidinyl]-4-fluorobenzoic acid in 50 ml of diethyl ether. Thereafter, a solution of 1.9 g of dicyclohexylcarbodiimide and 0.1 g of 4-pyrrolidinopyridine in 15 ml of diethyl ether is added dropwise over 10 minutes. The reaction mixture is stirred at room temperature for 12 hours. Subsequently, it is filtered and evaporated to dryness under reduced pressure. The residue is purified by chromatography on silica gel with n-hexane/diethyl ether (4:1) as the eluent. In this manner there is obtained 3-pentanone O-{2-chloro-5-[3,6-dihydro-2,6-dioxo-3-methyl-4 -trifluoromethyl-1(2H)-pyrimidinyl]-4-fluorobenzoyl}oxime, m.p. 128°-130° C.

후처리

  1. filtrationSubsequently, it is filtered
  2. customevaporated to dryness under reduced pressure
  3. customThe residue is purified by chromatography on silica gel with n-hexane/diethyl ether (4:1) as the eluent

출처 및 근거

ORD 기록
ord-e86122d1c61647a2b918633f26b6c004
출처 데이터셋
uspto-grants-1991_08
특허 번호
US05041156

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