Imidazole → HCID 86734684, compound

HRID 329008Notes

Reaction equation

HRID 329008 reaction equation
[C:1]1([C:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)(Cl)[C:8]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C(C2C=CC=CC=2)(Cl)C(Cl)=O)C=CC=CC=1.N1CCOCC1.[NH:46]1[CH:50]=[CH:49][N:48]=[CH:47]1>C(#N)C>[C:1]1([C:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:47]2[NH:46][CH:50]=[CH:49][N:48]=2)[C:8]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 8083MorpholineHCID 179412902-98-9HCID 1530310HCID 1530310, compound

Product 1

HCID 86734684HCID 86734684, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 15.5 g of diphenylchloroacetic acid morpholide, m.p. 113° C (prepared from diphenylchloroacetyl chloride and morpholine in accordance with the procedure described in Ber. 41, 3593) and 11g of imidazole in 100 ml of acetonitrile is heated at reflux for 18 hours. The solvent is removed by distillation in vacuo and, after addition of 70 ml of water, the residue is extracted with methylene chloride. The extracts are dried and the solvent is removed by distillation to yield diphenyl-imidazolylacetic acid morpholide which is further purified by recrystallization from methanol. The hydrochloride salt, m.p. 118° C, is obtained by treating an ethyl acetate solution of the free base with an ethereal solution of hydrogen chloride.

Workup

  1. temperatureat reflux for 18 hours
  2. customThe solvent is removed by distillation in vacuo
  3. additionafter addition of 70 ml of water
  4. extractionthe residue is extracted with methylene chloride
  5. customThe extracts are dried
  6. customthe solvent is removed by distillation

Sources & evidence

ORD record
ord-cba36c270d3940bdbf0189af13fa9635
Source dataset
uspto-grants-1977_04
Patent number
US04018924

Reaction notes

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