2-Amino-2-methyl-1-propanol → 2-(1-Chloro-2-methylpropan-2-yl)-4,4-dimethyl-4,5-dihydro-1,3-oxazole

HRID 1358622Notes

Reaction equation

HRID 1358622 reaction equation
[Cl:1][CH2:2][C:3]([CH3:8])([CH3:7])[C:4](Cl)=[O:5].[NH2:9][C:10]([CH3:14])([CH3:13])[CH2:11][OH:12]>C(Cl)(Cl)Cl>[CH3:7][C:3]([C:4]1[O:5][CH2:11][C:10]([CH3:14])([CH3:13])[N:9]=1)([CH3:8])[CH2:2][Cl:1].[OH:12][CH2:11][C:10]([NH:9][C:4](=[O:5])[C:3]([CH3:8])([CH3:7])[CH2:2][Cl:1])([CH3:14])[CH3:13]

Participants

5

Reactant 2

HCID 118072-Amino-2-methyl-1-propanolHCID 613453-Chloro-2,2-dimethylpropanoyl chloride

Product 2

HCID 159413362-(1-Chloro-2-methylpropan-2-yl)-4,4-dimethyl-4,5-dihydro-1,3-oxazoleHCID 18185421HCID 18185421, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

2-(1,1-dimethyl-2-chloroethyl)-4,4-dimethyl-2-oxazoline was prepared as follows. Initially, N-(2-hydroxy-1,1-dimethylethyl)-3-chloropivalamide was prepared by adding dropwise, at room temperature, a solution of 3-chloropivaloyl chloride (1.0 eq., 56 g, 0.36 mol) in CHCl3 (100 mL) to a stirred mixture of 2-amino-2-methyl-1-propanol (2.0 eq., 64.4 g, 0.72 mol) in CHCl3 (300 mL) over a period of one (1) hour. This mixture was allowed to auto-reflux for twenty (20) minutes and was then stirred overnight. The whitish-yellow precipitate that formed was gravity filtered, and the resulting yellow-brown solution was concentrated and purified by vacuum distillation (140-150° C., 1 mm Hg). The resulting yellow oil (61 g, 81%) was pure N-(2-hydroxy-1,1-dimethylethyl)-3-chloropivalamide as evidenced by 1H NMR (CDCl3): δ1.13 (s, 6H, CH3, CH3), 1.30 (s, 6H, CH3, CH3), 2.2 (br s, 1H, OH), 3.3 (s, 2H, CH2,—Cl), 3.6 (s, 2CH2—OH), 5.78 (br s, 1H, NH).

Workup

  1. additionby adding dropwise, at room temperature
  2. customThe whitish-yellow precipitate that formed
  3. filtrationfiltered
  4. concentrationthe resulting yellow-brown solution was concentrated
  5. distillationpurified by vacuum distillation (140-150° C., 1 mm Hg)

Sources & evidence

ORD record
ord-1df1d7bcb98f48bf8351a45a506651ad
Source dataset
uspto-grants-2003_07
Patent number
US06596798B1

Reaction notes

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