Triethylamine → HCID 19079219, compound

HRID 274643Notes

Reaction equation

HRID 274643 reaction equation
Cl.Cl.[NH2:3][CH2:4][CH2:5][CH2:6][S:7][C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1.C(N(CC)CC)C.[C:21]1([C:27]2[CH:35]=[CH:34][C:30]([C:31]([Cl:33])=[O:32])=[CH:29][CH:28]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(Cl)Cl>[ClH:33].[C:21]1([C:27]2[CH:28]=[CH:29][C:30]([C:31]([NH:3][CH2:4][CH2:5][CH2:6][S:7][C:8]3[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=3)=[O:32])=[CH:34][CH:35]=2)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 841514-Phenylbenzoyl chlorideHCID 190792594-(3-Aminopropylthio)pyridine dihydrochloride

Product 1

HCID 19079219HCID 19079219, compoundYield 67.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.00 g (4.15 mmol) of 4-(3-aminopropylthio)pyridine dihydrochloride and 2.89 ml (19.9 mmol) of triethylamine in 40 ml of methylene chloride was added 1.08 ml (4.98 mmol) of 4-phenylbenzoyl chloride under ice-cooling with stirring and the mixture was stirred at room temperature for 30 minutes. The reaction solution was washed with an aqueous saturated sodium bicarbonate solution and water and dried. The solvent was distilled off. The residue was purified by column chromatography (eluent: methanol/ethyl acetate=1:10) to obtain the powder which was washed with ether and dried to obtain 980 mg of the desired compound (free base) (67.8%, pale yellow powder), mp: 169.0°-170.0° C.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 30 minutes
  3. washThe reaction solution was washed with an aqueous saturated sodium bicarbonate solution and water
  4. customdried
  5. distillationThe solvent was distilled off
  6. customThe residue was purified by column chromatography (eluent: methanol/ethyl acetate=1:10)
  7. customto obtain the powder which
  8. washwas washed with ether
  9. customdried

Sources & evidence

ORD record
ord-ca4b124c586749e8a1bfe49e96f8159b
Source dataset
uspto-grants-1995_02
Patent number
US05389658

Reaction notes

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