Oxalyl chloride → 3-[3-(4,6-Diethoxy-2-pyrimidinyl)-1,2-benzisothiazol-5-yl]-1-methyl-6-(trifluoromethyl)uracil

HRID 49002

반응식

HRID 49002 반응식
[CH3:1][N:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5](=[O:12])[N:4]([C:13]2[CH:14]=[CH:15][C:16]3[S:20][N:19]=[C:18]([C:21](O)=O)[C:17]=3[CH:24]=2)[C:3]1=[O:25].C(Cl)(=O)C(Cl)=O.Cl.Cl.[C:34](=[NH:44])([O:41][CH2:42][CH3:43])[CH2:35][C:36](=[NH:40])[O:37][CH2:38][CH3:39].C(N(C(C)C)CC)(C)C>C(Cl)Cl.CN(C)C=O.C(OCC)C>[CH2:38]([O:37][C:36]1[CH:35]=[C:34]([O:41][CH2:42][CH3:43])[N:44]=[C:21]([C:18]2[C:17]3[CH:24]=[C:13]([N:4]4[C:5](=[O:12])[CH:6]=[C:7]([C:8]([F:11])([F:10])[F:9])[N:2]([CH3:1])[C:3]4=[O:25])[CH:14]=[CH:15][C:16]=3[S:20][N:19]=2)[N:40]=1)[CH3:39]

참가 물질

8

반응물 4

HCID 65578Oxalyl chlorideHCID 73106Diethyl malonimidateHCID 81531DiisopropylethylamineHCID 111878605-[3,6-Dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-carboxylic acid

생성물 1

HCID 206342213-[3-(4,6-Diethoxy-2-pyrimidinyl)-1,2-benzisothiazol-5-yl]-1-methyl-6-(trifluoromethyl)uracil수율 8.31%

시약·촉매·용매 3

HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매2회

실험 절차

To a cooled mixture of 5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-carboxylic acid (3.71 g, 10.0 mmol), diethyl ether and N,N-dimethylformamide (3.0 ml) is added oxalyl chloride (1.52 g, 12.0 mmol). The mixture is allowed to warm to room temperature and stirred overnight. The mixture is allowed to settle and the supernatant is decanted and concentrated in vacuo. The residue is taken up in methylene chloride and added dropwise to a stirred mixture of diethyl malonimidate dihydrochloride (2.31 g, 10.0 mmol), diisopropylethylamine (10 ml) and methylene chloride at −40° C. over one hour. The resultant mixture is allowed to warm to room temperature, diluted with methylene chloride, washed with water, 10% aqueous hydrochloric acid and water, dried over anhydrous magnesium sulfate and concentrated in vacuo to afford the title compound as a white solid (0.410 g, 8.31%, mp 197-200° C.) which is identified by NMR spectral analysis.

후처리

  1. customthe supernatant is decanted
  2. concentrationconcentrated in vacuo
  3. temperatureto warm to room temperature
  4. washwashed with water, 10% aqueous hydrochloric acid and water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-87586c6218434eba9d9754024c563445
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06706663B2

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