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

HRID 1803422ノート

反応式

HRID 1803422 の反応式
[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]

参加物

7

反応物 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59580681HCID 59580681、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-fdcf5ddab1344739b33278b5bfb9a7c8
出典データセット
uspto-grants-2013_01
特許番号
US08350044B2

反応ノート

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