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

HRID 1754332ノート

反応式

HRID 1754332 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

実験手順

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].

後処理

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

出典と根拠

ORDレコード
ord-efcfd1215f634c64b677ddbb32f28635
出典データセット
uspto-grants-2015_10
特許番号
US09169242B2

反応ノート

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