Sodium Bicarbonate → Ethyl 2-(2-aminothiazol-4-yl)-2-methoxyiminoacetate

HRID 364452ノート

反応式

HRID 364452 の反応式
[CH3:1][O:2][N:3]=[C:4]([C:10]([CH2:12]Cl)=O)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[NH2:14][C:15]([NH2:17])=[S:16].C([O-])(=O)C.[Na+].C(=O)(O)[O-].[Na+]>CO.O>[CH3:1][O:2][N:3]=[C:4]([C:10]1[N:14]=[C:15]([NH2:17])[S:16][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6]

参加物

7

反応物 4

HCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 2723790ThioureaHCID 3017525Ethyl 4-chloro-2-(methoxyimino)-3-oxobutanoate

生成物 1

HCID 581091Ethyl 2-(2-aminothiazol-4-yl)-2-methoxyiminoacetate収率 68.5%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

Ethyl 2-methoxyimino-4-chloroacetoacetate (syn isomer) (50 g.) was added over 3 minutes with stirring at ambient temperature to a solution of thiourea (18.4 g.) and sodium acetate (19.8 g.) in a mixture of methanol (250 ml.) and water (250 ml.). After stirring for 35 minutes at 40° to 45° C., the reaction mixture was cooled with ice and adjusted to pH 6.3 with a saturated aqueous solution of sodium bicarbonate. After stirring for 30 minutes at the same temperature, precipitates were collected by filtration, washed with water (200 ml.) and then with diisopropyl ether (100 ml.), and dried to give colorless crystals of ethyl 2-methoxyimino-2-(2-amino-1,3-thiazol-4-yl)acetate (syn isomer) (37.8 g.), m.p. 161° to 162° C.

後処理

  1. temperaturethe reaction mixture was cooled with ice
  2. stirringAfter stirring for 30 minutes at the same temperature
  3. customprecipitates
  4. filtrationwere collected by filtration
  5. washwashed with water (200 ml.)
  6. dry with materialwith diisopropyl ether (100 ml.), and dried

出典と根拠

ORDレコード
ord-3d85c218d8ac49c0ab39d0006b1d80ad
出典データセット
uspto-grants-1986_08
特許番号
US04604456

反応ノート

読み込み中…