Ethylene Oxide → 2-[Benzyl(2-hydroxyethyl)amino]benzamide

HRID 1439612Notes

Reaction equation

HRID 1439612 reaction equation
[CH2:1]([NH:8][C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([NH2:13])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:18]1[O:20][CH2:19]1>C(O)(=O)C>[CH2:1]([N:8]([CH2:18][CH2:19][OH:20])[C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([NH2:13])=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6354Ethylene OxideHCID 11345158HCID 11345158, compound

Product 1

HCID 203383632-[Benzyl(2-hydroxyethyl)amino]benzamide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

o-Benzylaminobenzamide (62 g) was added to a cold solution of 85 ml ethylene oxide in 500 ml acetic acid, the mixture stirred 22 hours at room temperature and concentrated on the rotovap to remove 250 ml acetic acid. The remainder was made alkaline with 10% NaOH and the solid filtered washed with water and recrystallized from 300 ml ethyl acetate to give 48.5 g. product, m.133-7°.

Workup

  1. concentrationconcentrated on the rotovap
  2. customto remove 250 ml acetic acid
  3. filtrationthe solid filtered
  4. washwashed with water
  5. customrecrystallized from 300 ml ethyl acetate
  6. customto give 48.5 g
  7. custom133-7°

Sources & evidence

ORD record
ord-6b167cf4c02242e99b2eb72f8e049521
Source dataset
uspto-grants-1977_11
Patent number
US04060526

Reaction notes

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