Benzoyl chloride → benzamide, N-(2-hydroxy-1,1-dimethylethyl)-

HRID 259094Notes

Reaction equation

HRID 259094 reaction equation
[NH2:1][C:2]([CH3:6])([CH3:5])[CH2:3][OH:4].[C:7](Cl)(=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>ClCCl>[C:7]([NH:1][C:2]([CH3:6])([CH3:5])[CH2:3][OH:4])(=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 118072-Amino-2-methyl-1-propanol

Product 1

HCID 639965benzamide, N-(2-hydroxy-1,1-dimethylethyl)-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 250 ml dichloromethane solution containing 89 g (1.0 mol) 2-amino-2-methyl-1-propanol at 0° was added dropwise with stirring 70 g (0.5 mol) benzoyl chloride in 250 ml dichloromethane. The reaction mixture was warmed to roome temperature and stirred for several hours. The 2-amino-2-methyl-1-propanol hydrochloride was removed from the reaction mixture by filtration and was thoroughly washed with dichloromethane. The filtrate and washings were combined and the dichloromethane removed under reduced pressure to afford 67.55 g (0.35 mol), 70%, 2-benzoylamino-2-methyl-1-propanol as a white solid, mp 80°-82°, sublimation at 75° (0.2 mm); ir (KBr) 1630 (c=o) cm-1 ; pmr (CDCl3) δ 1.50 (s, 6H), 3.67 (s, 2H), 5.27 (bs, 1H), 6.92 (bs, 1H) and 7.1 - 8.3 (m, 5H) ppm.

Workup

  1. additionwas added dropwise
  2. temperatureThe reaction mixture was warmed
  3. customThe 2-amino-2-methyl-1-propanol hydrochloride was removed from the reaction mixture by filtration
  4. washwas thoroughly washed with dichloromethane
  5. customthe dichloromethane removed under reduced pressure

Sources & evidence

ORD record
ord-3d534a8e6e624c878b542cd2fafca52c
Source dataset
uspto-grants-1977_07
Patent number
US04036843

Reaction notes

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