Ethanolamine → HCID 18185419, compound

HRID 1358621Notes

Reaction equation

HRID 1358621 reaction equation
[Cl:1][CH2:2][C:3]([CH3:8])([CH3:7])[C:4](Cl)=[O:5].[NH2:9][CH2:10][CH2:11][OH:12]>C(Cl)Cl>[CH3:7][C:3]([C:4]1[O:5][CH2:11][CH2:10][N:9]=1)([CH3:8])[CH2:2][Cl:1].[OH:12][CH2:11][CH2:10][NH:9][C:4](=[O:5])[C:3]([CH3:8])([CH3:7])[CH2:2][Cl:1]

Participants

5

Reactant 2

HCID 700EthanolamineHCID 613453-Chloro-2,2-dimethylpropanoyl chloride

Product 2

HCID 18185419HCID 18185419, compoundHCID 18185422HCID 18185422, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-(1,1-dimethyl-2-chloroethyl)-2-oxazoline was prepared as follows. Initially, N-(2-hydroxyethyl)-3-chloropivalamide was prepared by adding dropwise, at room temperature, a solution of 3-chloropivaloyl chloride (1.0 eq., 22.4 g, 0.14 mol) in CH2Cl2(100 mL) to a stirred mixture of 2-aminoethanol (2.0 eq., 17.6 g, 0.29 mol) in CH2Cl2(300 mL) over a period of one (1) hour. This mixture was allowed to auto-reflux for twenty (20) minutes and was then stirred for an additional forty (40) minutes. The whitish-yellow precipitate that formed was gravity filtered, and the resulting yellow solution was concentrated under vacuum. The resulting viscous yellow oil (23 g, 89% yield) was pure N-(2-hydroxyethyl)-3-chloropivalamide, as evidenced by 1H NMR (CDCl3): δ1.31 (s, 6H, CH3, CH3), 3.44 (q, 2H, CH2—NH), 3.61 (s, 2H, CH2—Cl), 3.73 (t, 2H, CH2—OH), 6.3 (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 solution was concentrated under vacuum

Sources & evidence

ORD record
ord-b5f7d2de42724dcca316cb96f3c6c138
Source dataset
uspto-grants-2003_07
Patent number
US06596798B1

Reaction notes

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