Ethanolamine → 4'-Chloro-2-(P-chlorophenyl)-2-[(hydroxyethyl)amino]acetophenone, hydrochloride

HRID 1381515Notes

Reaction equation

HRID 1381515 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:10]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)O)=[O:9])=[CH:4][CH:3]=1.[CH2:19]([CH2:21][NH2:22])[OH:20].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>CCOCC>[ClH:1].[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([CH:10]([NH:22][CH2:21][CH2:19][OH:20])[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[O:9])=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 700EthanolamineHCID 14812Phosphorus oxide (P4O10)HCID 2192861,2-Bis(4-chlorophenyl)-2-hydroxyethanone

Product 1

HCID 143911774'-Chloro-2-(P-chlorophenyl)-2-[(hydroxyethyl)amino]acetophenone, hydrochloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 4,4'-dichlorobenzoin (3.52 g, 0.0125 mole), ethanolamine (0.83 g, 0.0235 mole), and phosphorus pentoxide (0.10 g) was heated on a steam bath for 6 minutes with thorough mixing. After cooling, the reaction mixture was dissolved in ether and the ether solution decanted from the phosphorus pentoxide. The solution was treated with ethereal hydrogen chloride and the solid salt collected by filtration and washed with isopropyl ether. The solid was purified by trituration with acetonitrile. The white solid was collected, washed with isopropyl ether, and dried in a vacuum oven at 50° C. for two hours. The yield was 3.24 g (72%), m.p. 190°-193° C.

Workup

  1. temperaturewas heated on a steam bath for 6 minutes with thorough mixing
  2. temperatureAfter cooling
  3. customthe ether solution decanted from the phosphorus pentoxide
  4. additionThe solution was treated with ethereal hydrogen chloride
  5. filtrationthe solid salt collected by filtration
  6. washwashed with isopropyl ether
  7. customThe solid was purified by trituration with acetonitrile
  8. customThe white solid was collected
  9. washwashed with isopropyl ether
  10. customdried in a vacuum oven at 50° C. for two hours

Sources & evidence

ORD record
ord-c5b4631676d8410f9a46820872c87e89
Source dataset
uspto-grants-1989_02
Patent number
US04803200

Reaction notes

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