Water → Carbamic acid, N-(2-bromo-4-methyl-5-thiazolyl)-N-methyl-, 1,1-dimethylethyl ester

HRID 2199200노트

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HRID 2199200 반응식
[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1[S:12][C:11]([Br:13])=[N:10][C:9]=1[CH3:14])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].I[CH3:19].O>CN(C=O)C.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:15])[N:7]([C:8]1[S:12][C:11]([Br:13])=[N:10][C:9]=1[CH3:14])[CH3:19])([CH3:4])([CH3:3])[CH3:2]

참가 물질

7

반응물 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59580681HCID 59580681, 화합물

생성물 1

HCID 59580796Carbamic acid, N-(2-bromo-4-methyl-5-thiazolyl)-N-methyl-, 1,1-dimethylethyl ester수율 54%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of (2-bromo-4-methyl-thiazol-5-yl)-carbamic acid tert-butyl ester (2.93 g, 10 mmol) in DMF (50 mL) at 0° C. was added NaH (480 mg, 12 mmol, 60% dispersion in mineral oil) in one portion and the suspension was stirred for 1 h. Iodomethane (0.65 mL, 10.5 mmol) was added in one portion, and after 5 min the reaction mixture was warmed to ambient temperature and stirred for 5 h. Water and ethyl acetate were added and the resulting biphasic mixture was separated. The aqueous layer was extracted one time with ethyl acetate. The combined organic extracts were washed twice with brine, dried over Na2SO4, filtered and concentrated to dryness under reduced pressure. The crude product was purified by silica gel chromatography (0-100% ethyl acetate/hexanes) to give the desired product as a clear oil (1.66 g, 54%): IR (KBr) 1688 cm−1; 1H NMR (300 MHz, CDCl3) δ 2.98 (s, 3H), 2.29 (s, 3H), 1.54 (s, 9H); ESIMS m/z 309 (M+2).

후처리

  1. stirringstirred for 5 h
  2. customthe resulting biphasic mixture was separated
  3. extractionThe aqueous layer was extracted one time with ethyl acetate
  4. washThe combined organic extracts were washed twice with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure
  8. customThe crude product was purified by silica gel chromatography (0-100% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-35934fd7149747138a80a78516e02cde
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09357780B2

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