Water → 4-[2-(tert-Butyl-diphenyl-silanyloxy)-1,1-dimethyl-ethyl]-thiazol-2-ylamine

HRID 1809423ノート

反応式

HRID 1809423 の反応式
Br[CH2:2][C:3](=O)[C:4]([CH3:25])([CH3:24])[CH2:5][O:6][Si:7]([C:20]([CH3:23])([CH3:22])[CH3:21])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[NH2:27][C:28]([NH2:30])=[S:29].O>C(#N)C>[C:20]([Si:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[O:6][CH2:5][C:4]([C:3]1[N:27]=[C:28]([NH2:30])[S:29][CH:2]=1)([CH3:25])[CH3:24])([CH3:23])([CH3:22])[CH3:21]

参加物

5

反応物 3

HCID 962WaterHCID 2723790ThioureaHCID 592679781-Bromo-4-(tert-butyl-diphenyl-silanyloxy)-3,3-dimethyl-butan-2-one

生成物 1

HCID 592680294-[2-(tert-Butyl-diphenyl-silanyloxy)-1,1-dimethyl-ethyl]-thiazol-2-ylamine収率 6.1%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A solution of 1-bromo-4-(tert-butyl-diphenyl-silanyloxy)-3,3-dimethyl-butan-2-one (40 g, 92.3 mmol) and thiourea (8.4 g, 110.5 mmol) in 400.0 mL of acetonitrile is heated under reflux for 4 h. After cooling the reaction mixture to room temperature, water is added and the aqueous layer is extracted with ethyl acetate; the organic layer is dried over anhydrous Na2SO4, filtered and the solvent is removed under reduced pressure to afford the crude product that is purified by silica gel chromatography to afford 2.3 g of 4-[2-(tert-Butyl-diphenyl-silanyloxy)-1,1-dimethyl-ethyl]-thiazol-2-ylamine as a light brown solid. Yield: 4%, over two steps; 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.00 (9H, s), 1.25 (6H, s), 3.62 (2H, s), 5.60 (2H, s), 6.15 (1H, s), 7.25-7.40 (6H, m), 7.50-7.60 (4H, m); m/z 411 [M+H].

後処理

  1. temperatureunder reflux for 4 h
  2. extractionthe aqueous layer is extracted with ethyl acetate
  3. dry with materialthe organic layer is dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. customthe solvent is removed under reduced pressure
  6. customto afford the crude product that
  7. customis purified by silica gel chromatography

出典と根拠

ORDレコード
ord-75ae579b91d2419dae22caa709e3e4ab
出典データセット
uspto-grants-2013_01
特許番号
US08362039B2

反応ノート

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