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Benzoyl chloride → HCID 20322593, compound

HRID 840006
Notes
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Reaction equation

HRID 840006 reaction equation
[CH2:1]([C:3]1([CH3:30])[N:22]([CH2:23][CH2:24][OH:25])[C:21]([CH2:27][CH3:28])([CH3:26])[CH2:20][C:5]2([NH:9][C:8](=[O:10])[N:7]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:6]2=[O:19])[CH:4]1[CH3:29])[CH3:2].C(N(CC)CC)C.[C:38](Cl)(=[O:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.C(=O)([O-])[O-].[K+].[K+]>C1C=CC=CC=1>[C:38]([O:25][CH2:24][CH2:23][N:22]1[C:21]([CH2:27][CH3:28])([CH3:26])[CH2:20][C:5]2([NH:9][C:8](=[O:10])[N:7]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:6]2=[O:19])[CH:4]([CH3:29])[C:3]1([CH2:1][CH3:2])[CH3:30])(=[O:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 20322512HCID 20322512, compound

Product 1

HCID 20322593HCID 20322593, compoundYield 49.9%

Reagents, catalysts & solvents 1

HCID 241
Benzene
Solvent

Procedure

To a solution of 2.5 g of the oily product obtained in Example 6 in 30 ml of benzene were added 1.2 g of triethylamine; 0.8 g of benzoyl chloride was then added dropwise with ice-cooling. The mixture was refluxed by heating for 2 hours and, after cooling, an aqueous solution of potassium carbonate was added. The mixture was extracted with benzene. The extract was washed with water, dried over anhydrous sodium sulphate and then concentrated by evaporation under reduced pressure. The resulting oily product was first purified by column chromatography on silica gel (eluent: a 10 : 0.5 by volume mixture of hexane and triethylamine) and then by recrystallization from diethyl ether, giving 1.5 g of Compound 130 as crystals melting at 123° - 124.5° C.

Workup

  1. temperaturecooling
  2. temperatureThe mixture was refluxed
  3. temperatureby heating for 2 hours
  4. temperatureafter cooling
  5. extractionThe mixture was extracted with benzene
  6. washThe extract was washed with water
  7. dry with materialdried over anhydrous sodium sulphate
  8. concentrationconcentrated by evaporation under reduced pressure
  9. customThe resulting oily product was first purified by column chromatography on silica gel (eluent
  10. additiona 10 : 0.5 by volume mixture of hexane and triethylamine) and then
  11. customby recrystallization from diethyl ether

Sources & evidence

ORD record
ord-eee529cebfe44457a89ddf6876bd5306
Source dataset
uspto-grants-1978_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04097587

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes