Chloroform → HCID 67851179, compound

HRID 1197665Notes

Reaction equation

HRID 1197665 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:26])=[C:5]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)[CH:6]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)[C:7]=1[C:8]([OH:10])=[O:9].[CH2:27](O)[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].C1(N=C=NC2CCCCC2)CCCCC1.C(Cl)(Cl)Cl>C1(C)C=CC=CC=1>[CH3:1][C:2]1[NH:3][C:4]([CH3:26])=[C:5]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)[CH:6]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)[C:7]=1[C:8]([O:10][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[O:9]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 81031-HexanolHCID 10868DicyclohexylcarbodiimideHCID 19107423HCID 19107423, compound

Product 1

HCID 67851179HCID 67851179, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

350 mg (1 mmol) of 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-5-pyridylpyridine-3-carboxylic acid, 102 mg (1 mmol) of hexyl alcohol, 309 mg (1.4 mmol) of N,N'-dicyclohexylcarbodiimide, 134 mg (1.1 mmol) of 4-N,N-dimethylaminopyridine were dissolved in 10 ml of toluene, with application of heat thereto. This reaction mixture was refluxed with application of heat for 1 hour, and then cooled to room temperature. To this reaction mixture, 20 ml of chloroform was added. The reaction mixture was then washed with water and dried over anhydrous sodium sulfate. The solvents contained in the reaction mixture were then distilled of and the residue was chromatographed on a silica gel column, whereby the captioned compound was obtained. The yield was 389 mg (89.5%).

Workup

  1. temperatureof heat
  2. temperatureThis reaction mixture was refluxed with application
  3. temperatureof heat for 1 hour
  4. washThe reaction mixture was then washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationwere then distilled of and the residue
  7. customwas chromatographed on a silica gel column, whereby the captioned compound
  8. customwas obtained

Sources & evidence

ORD record
ord-1db1e452090847b6b3728e7d71378b16
Source dataset
uspto-grants-1994_01
Patent number
US05276150

Reaction notes

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