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

HRID 1754332Notes

Reaction equation

HRID 1754332 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

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].

Workup

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

Sources & evidence

ORD record
ord-efcfd1215f634c64b677ddbb32f28635
Source dataset
uspto-grants-2015_10
Patent number
US09169242B2

Reaction notes

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