Oxalyl chloride → (Z)-5-Fluoro-2-methyl-1-(4-methylthiobenzylidene)inden-3-ylmethyl isocyanate

HRID 1420729ノート

反応式

HRID 1420729 の反応式
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)/[C:7](=[CH:11]\[C:12]1[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=1)/[C:6]([CH3:20])=[C:5]2[CH2:21]C(O)=O.[C:25](Cl)(=[O:29])C(Cl)=O.C[Si]([N:35]=[N+]=[N-])(C)C>C(Cl)Cl.CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)/[C:7](=[CH:11]\[C:12]1[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=1)/[C:6]([CH3:20])=[C:5]2[CH2:21][N:35]=[C:25]=[O:29]

参加物

6

反応物 3

HCID 65578Oxalyl chlorideHCID 78378AzidotrimethylsilaneHCID 5352624Sulindac Sulfide

生成物 1

HCID 86745524(Z)-5-Fluoro-2-methyl-1-(4-methylthiobenzylidene)inden-3-ylmethyl isocyanate

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒

実験手順

To a suspension of (Z)-5-fluoro-2-methyl-1-(4-methylthiobenzylidene)inden-3-ylacetic acid (5.0 g, 14.7 mmol) in methylene chloride (50 mL) at room temperature there was added oxalyl chloride (2.8 g, 22 mmol) and DMF (2 drops) and the mixture stirred for 1 hour; the solution was evaporated and the crude acid chloride flushed twice with carbon tetrachloride (20 mL) then suspended in carbon tetrachloride (25 mL) and trimethylsilyl azide (2.53 g, 22 mmol) was added. The mixture was stirred at room temperature for 15 minutes, then gently heated on a steam bath as nitrogen was evolved. The heating was continued until gas evolution ceased, then the mixture was evaporated to afford the crude title compound as an oil which was used as such in the next step.

後処理

  1. customthe solution was evaporated
  2. customthe crude acid chloride flushed twice with carbon tetrachloride (20 mL)
  3. stirringThe mixture was stirred at room temperature for 15 minutes
  4. temperaturegently heated on a steam bath as nitrogen
  5. customthe mixture was evaporated

出典と根拠

ORDレコード
ord-d5c63418825a47f08d378d926eb469e3
出典データセット
uspto-grants-2000_06
特許番号
US06071934

反応ノート

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