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Dimethylformamide → HCID 14230767、化合物

HRID 621055
ノート
印刷プレビュー

反応式

HRID 621055 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 7841Allyl bromide2 回HCID 11430Potassium Carbonate2 回HCID 13338941HCID 13338941、化合物

生成物 1

HCID 14230767HCID 14230767、化合物収率 91.1%

試薬・触媒・溶媒 1

HCID 962Water
溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-bf9b91fe3242484ea2ea2f988a552c7b
出典データセット
uspto-grants-1989_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04822790

反応ノート

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このページの内容参加物実験手順後処理出典と根拠反応ノート