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

HRID 1802420노트

반응식

HRID 1802420 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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].

후처리

  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

출처 및 근거

ORD 기록
ord-2eb1f920f2a34e1ebad9d587c191b9a1
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08349871B2

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