Methyl iodide → N-(6-benzyloxy-3-methoxy-2,2-dimethylchroman-4-yl)-N-methyl-methanesulfonamide

HRID 613440노트

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HRID 613440 반응식
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[O:15][C:14]([CH3:20])([CH3:19])[CH:13]([OH:21])[CH:12]2[N:22]([CH3:27])[S:23]([CH3:26])(=[O:25])=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:30]I>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[O:15][C:14]([CH3:20])([CH3:19])[CH:13]([O:21][CH3:30])[CH:12]2[N:22]([CH3:27])[S:23]([CH3:26])(=[O:24])=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 11760985N-(6-benzyloxy-3-hydroxy-2,2-dimethylchroman-4-yl)-N-methyl-methanesulfonamide

생성물 1

HCID 19593330N-(6-benzyloxy-3-methoxy-2,2-dimethylchroman-4-yl)-N-methyl-methanesulfonamide수율 98.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

0.5 g (1.3 mmol) of N-(6-benzyloxy-3-hydroxy-2,2-dimethylchroman-4-yl)-N-methyl-methanesulfonamide (Example 1g) dissolved in 4 ml of DMF was added dropwise to a suspension of 0.05 g (1.7 mmol) of sodium hydride in 3 ml of DMF. The mixture was stirred at RT for 30 min, 0.25 g (1.8 mmol) of methyl iodide was added, and the mixture was stirred at RT for another 3 h. The reaction mixture was concentrated under reduced pressure, the residue was taken up in water and EA and the organic phase was washed with dilute hydrochloric acid and saturated sodium bicarbonate solution. Drying over magnesium sulfate and concentration under reduced pressure gave 0.52 g of N-(6-benzyloxy-3-methoxy-2,2-dimethylchroman-4-yl)-N-methyl-methanesulfonamide, m.p. 119-121° C.

후처리

  1. stirringthe mixture was stirred at RT for another 3 h
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. washEA and the organic phase was washed with dilute hydrochloric acid and saturated sodium bicarbonate solution
  4. dry with materialDrying over magnesium sulfate and concentration under reduced pressure

출처 및 근거

ORD 기록
ord-86930d6d98734119bdcd1261ef25beb1
출처 데이터셋
uspto-grants-1999_12
특허 번호
US06008245

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