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

HRID 379628노트

반응식

HRID 379628 반응식
[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]

참가 물질

6

반응물 3

HCID 65578Oxalyl chlorideHCID 78378AzidotrimethylsilaneHCID 5352624Sulindac Sulfide

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2c29484572e74404aa1f599f71c996ec
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06300346B1

반응 노트

불러오는 중…