Triethylamine → HCID 86737276, compound

HRID 903909Notes

Reaction equation

HRID 903909 reaction equation
[C:1]([OH:20])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C(N(CC)CC)C.ClC(OCC)=O.Cl.Cl.[CH2:36]([NH:43][NH2:44])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>C(Cl)Cl>[CH2:36]([NH:43][NH:44][C:1](=[O:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 10928Ethyl chloroformateHCID 146540Benzylhydrazine dihydrochlorideHCID 5280450Linoleic Acid

Product 1

HCID 86737276HCID 86737276, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7.0 g linoleic acid in 250 ml methylenechloride cooled to -20° is added first 2.5 g triethylamine and then dropwise 2.7 g ethyl chloroformate. The reaction mixture is allowed gradually to come to room temperature and stirred for 2 hours. There is then added 5.0 g triethylamine followed by 4.9 g benzylhydrazine dihydrochloride and the reaction mixture then stirred for 16 hours. Thereafter the reaction mixture is extracted five times with portions of 2 N hydrochloric acid, then once with 2 N aqueous sodium hydroxide solution and washed extensively with saturated aqueous sodium chloride. The organic phase is then dried with anh. sodium sulphate, filtered and the filtrate evaporated i.v. to dryness. The residue is then chromatographed over silica gel, with chloroform as the eluent. The desired fractions* are collected, and evaporated i.v. to dryness to yield the title product as a viscous oil.

Workup

  1. customto come to room temperature
  2. stirringthe reaction mixture then stirred for 16 hours
  3. extractionThereafter the reaction mixture is extracted five times with portions of 2 N hydrochloric acid
  4. washonce with 2 N aqueous sodium hydroxide solution and washed extensively with saturated aqueous sodium chloride
  5. dry with materialThe organic phase is then dried with anh. sodium sulphate
  6. filtrationfiltered
  7. customthe filtrate evaporated i.v
  8. customThe residue is then chromatographed over silica gel, with chloroform as the eluent
  9. customThe desired fractions* are collected
  10. customevaporated i.v

Sources & evidence

ORD record
ord-9467057db89e4417bc6f7f25b96c9b9e
Source dataset
uspto-grants-1980_10
Patent number
US04229463

Reaction notes

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