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Dimethylformamide → HCID 14230767, 화합물

HRID 621147
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HRID 621147 반응식
CN(C)C=O.[C:6]([NH:25][C:26]1[S:27][CH:28]=[C:29](/[C:31](=[N:36]/[OH:37])/[C:32]([O:34][CH3:35])=[O:33])[N:30]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:44](Br)[CH:45]=[CH2:46]>O>[C:6]([NH:25][C:26]1[S:27][CH:28]=[C:29](/[C:31](=[N:36]/[O:37][CH2:46][CH:45]=[CH2:44])/[C:32]([O:34][CH3:35])=[O:33])[N:30]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 7841Allyl bromide2회HCID 11430Potassium Carbonate2회HCID 13338941HCID 13338941, 화합물

생성물 1

HCID 14230767HCID 14230767, 화합물수율 91.1%

시약·촉매·용매 1

HCID 962Water
용매

실험 절차

To 70.5 ml of N,N-dimethylformamide are added 7.05 g of methyl 2-(2-tritylamino-4-thiazolyl)-(Z)-2-hydroxyiminoacetate and 3.3 g of potassium carbonate. Then, under ice-cooling and stirring 2.12 g of allyl bromide is added dropwise over a period of 5 minutes. The mixture is further stirred under ice-cooling for 4 hours. To this reaction mixture are added 1.65 g of potassium carbonate and 1.06 g of allyl bromide, and the mixture is stirred for an additional 4 hours. The reaction mixture is diluted with 150 ml of water and extracted three times with 100 ml portions of ether. The ether extract is washed twice with 100 ml portios of aqueous sodium chloride and dried over anhydrous sodium sulfate. The solvent is then distilled off and the residue is purified by column chromatography [silica gel: 300 g; eluent: hexane-ethyl acetate (1:1)] and crystallized from ether-hexane to give 7.0 g of methyl 2-(2-tritylamino-4-thiazolyl)-(Z)-2-allyloxyiminoacetate, m.p. 115°- 116° C.

후처리

  1. temperatureThen, under ice-cooling
  2. additionis added dropwise over a period of 5 minutes
  3. temperaturecooling for 4 hours
  4. stirringthe mixture is stirred for an additional 4 hours
  5. extractionextracted three times with 100 ml portions of ether
  6. extractionThe ether extract
  7. washis washed twice with 100 ml portios of aqueous sodium chloride
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationThe solvent is then distilled off
  10. customthe residue is purified by column chromatography [silica gel: 300 g; eluent: hexane-ethyl acetate (1:1)]
  11. customcrystallized from ether-hexane

출처 및 근거

ORD 기록
ord-22b9f7cd00444dfd84d2fe80ef907b76
출처 데이터셋
uspto-grants-1989_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04822788

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