Oxalyl chloride → HCID 23152653, compound

HRID 1012314Notes

Reaction equation

HRID 1012314 reaction equation
[CH:1]1([C:7]2[C:8]3[CH:24]=[CH:23][C:22]([C:25]([OH:27])=O)=[CH:21][C:9]=3[N:10]3[C:16]=2[C:15]2[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=2[O:13][CH2:12][CH2:11]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)(=O)C([Cl:31])=O>C(Cl)(Cl)Cl.CN(C)C=O>[CH:1]1([C:7]2[C:8]3[CH:24]=[CH:23][C:22]([C:25]([Cl:31])=[O:27])=[CH:21][C:9]=3[N:10]3[C:16]=2[C:15]2[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=2[O:13][CH2:12][CH2:11]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 11994755HCID 11994755, compound

Product 1

HCID 23152653HCID 23152653, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6212ChloroformSolvent

Procedure

To a solution of 12-cyclohexyl-6,7-dihydro-5-oxa-7a-azadibenzo[a,e]azulene-9-carboxylic acid (500 mg, 1.38 mmol) in chloroform (10 ml) were added oxalyl chloride (0.15 ml, 1.66 mmol) and several drops of N,N-dimethylformamide. The mixture was stirred at room temperature for 2 hr and concentrated. Hexane was added to the obtained residue, and the precipitated solid was collected by filtration. The solid was washed with hexane to give 12-cyclohexyl-6,7-dihydro-5-oxa-7a-azadibenzo[a,e]azulene-9-carbonyl chloride (476 mg, yield 91%).

Workup

  1. concentrationconcentrated
  2. additionHexane was added to the obtained residue
  3. filtrationthe precipitated solid was collected by filtration
  4. washThe solid was washed with hexane

Sources & evidence

ORD record
ord-f178458422294b36989fee36c2c2c811
Source dataset
uspto-grants-2011_07
Patent number
US07977331B1

Reaction notes

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