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Triethylamine → 5-oxo-2,2,4-trimethyl-3-thiazoline O-[N-(N-methylfluoroformamidothio)-N-methylcarbamoyl]oxime

HRID 1981374
ノート
印刷プレビュー

反応式

HRID 1981374 の反応式
C(N(CC)CC)C.[N:8](=[C:10]1[S:14][C:13]([CH3:16])([CH3:15])[N:12]=[C:11]1[CH3:17])[OH:9].[CH3:18][N:19]([S:23][N:24]([CH3:28])[C:25](F)=[O:26])[C:20]([F:22])=[O:21]>C1(C)C=CC=CC=1>[CH3:18][N:19]([S:23][N:24]([CH3:28])[C:25]([O:9][N:8]=[C:10]1[S:14][C:13]([CH3:16])([CH3:15])[N:12]=[C:11]1[CH3:17])=[O:26])[C:20]([F:22])=[O:21]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8471TriethylamineHCID 12897270bis-(N-methyl-N-fluorocarbonylamino)sulfideHCID 1362290545-Oxo-2,2,4-trimethyl-3-thiazoline oxime

生成物 1

HCID 538867305-oxo-2,2,4-trimethyl-3-thiazoline O-[N-(N-methylfluoroformamidothio)-N-methylcarbamoyl]oxime

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
-50 °C

実験手順

8.3 ml of triethylamine are added dropwise to a suspension of 8.59 g of 5-oxo-2,2,4-trimethyl-3-thiazoline oxime in a solution of 10.0 g of bis-(N-methyl-N-fluorocarbonylamino)sulfide in 100 ml of absolute toluene, cooled to -50° C. The resulting clear solution is allowed to warm slowly to 0° C. during 11/2 hours, during which time a crystalline product is precipitated. The reaction mixture is poured into ice-cold brine and extracted with ethyl acetate. After drying the organic phase over anhydrous sodium sulfate and evaporating it, the resulting residue is purified by chromatography on silica gel (eluent:ethyl acetate/n-hexane 1:1). Crystallization from ethyl acetate/n-hexane yields 5-oxo-2,2,4-trimethyl-3-thiazoline O-[N-(N-methylfluoroformamidothio)-N-methylcarbamoyl]oxime, m.p. 77°-79° C.

後処理

  1. temperatureto warm slowly to 0° C. during 11/2 hours
  2. customduring which time a crystalline product is precipitated
  3. additionThe reaction mixture is poured into ice-cold brine
  4. extractionextracted with ethyl acetate
  5. dry with materialAfter drying the organic phase over anhydrous sodium sulfate
  6. customevaporating it
  7. customthe resulting residue is purified by chromatography on silica gel (eluent:ethyl acetate/n-hexane 1:1)
  8. customCrystallization from ethyl acetate/n-hexane

出典と根拠

ORDレコード
ord-2f5c88dbb8f24077b1f30030dd6ef7ad
出典データセット
uspto-grants-1985_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04514566

反応ノート

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