Dimethylformamide → (2Z)-2-[2-(dimethylaminomethylideneamino)-1,3-thiazol-4-yl]-2-methoxyiminoacetyl chloride;hydrochloride

HRID 266246

反応式

HRID 266246 の反応式
[CH3:1][N:2]([CH3:5])[CH:3]=O.C(Cl)(=O)C([Cl:9])=O.[NH2:12][C:13]1[S:14][CH:15]=[C:16](/[C:18](=[N:22]/[O:23][CH3:24])/[C:19](O)=[O:20])[N:17]=1>O1CCCC1>[ClH:9].[CH3:1][N:2]([CH:3]=[N:12][C:13]1[S:14][CH:15]=[C:16](/[C:18](=[N:22]/[O:23][CH3:24])/[C:19]([Cl:9])=[O:20])[N:17]=1)[CH3:5]

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 5486924(alphaZ)-2-Amino-alpha-(methoxyimino)-4-thiazoleacetic acid

生成物 1

HCID 140382097(2Z)-2-[2-(dimethylaminomethylideneamino)-1,3-thiazol-4-yl]-2-methoxyiminoacetyl chloride;hydrochloride収率 43%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-15 °C

実験手順

Dimethylformamide (1.6 g, 22 mmol) and 10 ml of tetrahydrofuran were mixed, to which 3.06 g (24 mmol) of oxalyl chloride were added dropwise under ice-cooling. After completion of the dropwise addition, the resulting mixture was stirred for further 10 minutes and was then cooled to -15° C. To the mixture so obtained, were added 2.0 g (10 mmol) of (Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetic acid and 10 ml of tetrahydrofuran, followed by stirring for 80 minutes. The reaction mixture was concentrated under reduced pressure. Slurry was collected by filtration under a nitrogen gas stream and then dried at room temperature, whereby 1.32 g of the title compound were obtained (yield: 43%).

後処理

  1. additionwere added dropwise under ice-
  2. temperaturecooling
  3. additionAfter completion of the dropwise addition
  4. customTo the mixture so obtained
  5. stirringby stirring for 80 minutes
  6. concentrationThe reaction mixture was concentrated under reduced pressure
  7. filtrationSlurry was collected by filtration under a nitrogen gas stream
  8. customdried at room temperature

出典と根拠

ORDレコード
ord-43c0ae2acb1b4efd89b9f833e53f78b2
出典データセット
uspto-grants-1997_07
特許番号
US05650518

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