2-Amino-2-methyl-1-propanol → 3-bromo-N-(1-hydroxy-2-methylpropan-2-yl)-4-methylbenzamide

HRID 1754332노트

반응식

HRID 1754332 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5](Cl)=[O:6].[NH2:12][C:13]([CH3:17])([CH3:16])[CH2:14][OH:15]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([NH:12][C:13]([CH3:17])([CH3:16])[CH2:14][OH:15])=[O:6]

참가 물질

4

반응물 2

HCID 118072-Amino-2-methyl-1-propanolHCID 27570573-Bromo-4-methylbenzoyl chloride

생성물 1

HCID 675153193-bromo-N-(1-hydroxy-2-methylpropan-2-yl)-4-methylbenzamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

To a stirred 0° C. cooled solution of 3-bromo-4-methylbenzoyl chloride (prepared from the corresponding carboxylic acid; 1.40 g, 6.04 mmol, 1.0 eq) in DCM (10 mL), was added a solution of 2-amino-2-methylpropanol (1.44 mL, 15.11 mmol, 2.5 eq) in DCM (10 mL) drop wise for 15 min and then warmed to room temperature. After stirring for 24 h at room temperature, the reaction mixture was diluted with DCM (50 mL) and the organic layer was washed with water (20 mL) followed by brine (20 mL), dried (Na2SO4) and filtered. The filtrate was concentrated under vacuum to afford the 1.7 g of the desired product as a white solid. 1HNMR (400 MHz, DMSO-d6) δ 8.00 (d, J=1.0 Hz, 1H), 7.70 (dd, J=1.0, 8.0 Hz, 1H), 7.62 (s, 1H, D2O exchangeable), 7.40 (d, J=8.0 Hz, 1H), 4.85 (t, J=6.0 Hz, 1H, D2O exchangeable), 3.49 (d, J=6.0 Hz, 2H), 2.37 (s, 3H), 1.28 (s, 6H); ESI-MS (m/z) 286, 288 [(MH)+, Br79,81].

후처리

  1. washthe organic layer was washed with water (20 mL)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under vacuum

출처 및 근거

ORD 기록
ord-efcfd1215f634c64b677ddbb32f28635
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09169242B2

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