Bromoacetic Acid → HCID 85527358, compound

HRID 364183Notes

Reaction equation

HRID 364183 reaction equation
[Br:1][CH2:2][C:3]([OH:5])=[O:4].C(N(CC)C(C)C)(C)C.[CH2:15]([NH:22][CH2:23][CH2:24][O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(#N)C>[BrH:1].[C:27]1([CH2:26][O:25][CH2:24][CH2:23][N:22]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:2][C:3]([OH:5])=[O:4])[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 6227Bromoacetic Acid2×HCID 81531DiisopropylethylamineHCID 5624481-Benzylamino-2-benzyloxyethane

Product 1

HCID 85527358HCID 85527358, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 13.8 g of bromoacetic acid, 200 ml of acetonitrile, 19.0 ml. of N,N-diisopropylethylamine, anmd 26.3 g of N,O-dibenzylethanolamine was heated for 24 hours under reflux. An additional portion of bromoacetic acid (3.5 g) was added, and heating continued for an additional 24 hours. Refrigeration of the resulting mixture caused the precipitation of the title compound as white needles of mp 115°-117° C. after recrystallization from ethyl acetate.

Workup

  1. temperatureunder reflux
  2. temperatureheating
  3. customthe precipitation of the title compound as white needles of mp 115°-117° C.
  4. customafter recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-3d7e64c756e04547ac2005824351de7d
Source dataset
uspto-grants-1986_08
Patent number
US04604390

Reaction notes

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