Ethanolamine → HCID 4610719, compound

HRID 355459Notes

Reaction equation

HRID 355459 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:13]=[CH:12][C:8]([C:9](Cl)=[O:10])=[CH:7][CH:6]=1)=[O:4].[NH2:14][CH2:15][CH2:16][OH:17]>C(Cl)Cl>[OH:17][CH2:16][CH2:15][NH:14][C:9](=[O:10])[C:8]1[CH:12]=[CH:13][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 700EthanolamineHCID 81850Methyl 4-(chlorocarbonyl)benzoate

Product 1

HCID 4610719HCID 4610719, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Into an ice-cooled and stirred solution of 4-methoxycarbonylbenzoyl chloride 1 (53.6 g, 0.270 mol) in methylene chloride was dropwisely added a solution of 2-aminoethanol (36.3 g, 0.594 mol) in methylene chloride (40 ml) under nitrogen during 1 hr, and the mixture was stirred for 3 hr at room temperature. The resulting precipitate was collected by vacuum filtration, washed thoroughly with water and dried in vacuo at 50° C. to give N-(2-hydroxyethyl)-4-methoxycarbonylbenzamide 2 (53.3 g, 88% yield) as white powder: 1H NMR (CD3SOCD3)δ3.45 (t of t, 2H, J=5.4 and 5.9 Hz, CH2N), 3.64 (t, 2H, J=5.9 Hz, CH2 O), 3.90 (s, 3H, CH3O), 4.87 (brs, 1H, OH), 8.02 (d, 2H, J=9.3 Hz, 2,6-Ar-H), 8.05 (d, 2H, J=9.3 Hz, 3,5-Ar-H), 8.65 (t, 1H, J=5.4 Hz, NH).

Workup

  1. filtrationThe resulting precipitate was collected by vacuum filtration
  2. washwashed thoroughly with water
  3. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-fbe676b720714f6cbda9e630dc398fea
Source dataset
uspto-grants-1998_11
Patent number
US05830948

Reaction notes

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