Ethanolamine → HCID 18974079, compound

HRID 2395037Notes

Reaction equation

HRID 2395037 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH:15]=[CH:16][C:17]1[CH:22]=[CH:21][C:20]([C:23](Cl)=[O:24])=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:26][CH2:27][CH2:28][OH:29]>ClCCl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1/[CH:15]=[CH:16]/[C:17]1[CH:22]=[CH:21][C:20]([C:23]([NH:26][CH2:27][CH2:28][OH:29])=[O:24])=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 700EthanolamineHCID 54444037HCID 54444037, compound

Product 1

HCID 18974079HCID 18974079, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 4-[2-(2-benzyloxyphenyl)ethenyl]-benzenecarbonyl chloride (0.98 g) in dichloromethane (5 ml) was added dropwise to a solution of 2-aminoethanol (0.51 ml) in dichloromethane (15 ml) maintained at 0° C. The reaction mixture was allowed to warm to ambient temperature and was stirred for 16 hours. The reaction mixture was washed with water (20 ml) and saturated aqueous sodium bicarbonate (20 ml) and dried. Evaporation of the solvent left a solid residue which was crystallised twice from methanol to give (E)-4-[2-(2-benzyloxyphenyl)ethenyl]-N-(2-hydroxyethyl)benzenecarboxamide (m.p. 149°-151° C.; yield 19%) containing about 4% of the related Z-isomer.

Workup

  1. temperatureto warm to ambient temperature
  2. washThe reaction mixture was washed with water (20 ml) and saturated aqueous sodium bicarbonate (20 ml)
  3. customdried
  4. customEvaporation of the solvent
  5. waitleft a solid residue which
  6. customwas crystallised twice from methanol

Sources & evidence

ORD record
ord-9670e8dbc9a04ba6878a662ce085157b
Source dataset
uspto-grants-1998_09
Patent number
US05811459

Reaction notes

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