Phosphorus oxychloride → HCID 22627454, compound

HRID 278115Notes

Reaction equation

HRID 278115 reaction equation
P(Cl)(Cl)(Cl)=O.[Cl:6][C:7]1[CH:31]=[CH:30][CH:29]=[CH:28][C:8]=1[CH2:9][N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:19]([NH2:21])=O)[CH:17]=2)[C:12]([C:22](=[O:25])[CH2:23][CH3:24])=[C:11]1[CH2:26][CH3:27].O.N>CN(C)C=O>[Cl:6][C:7]1[CH:31]=[CH:30][CH:29]=[CH:28][C:8]=1[CH2:9][N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:19]#[N:21])[CH:17]=2)[C:12]([C:22](=[O:25])[CH2:23][CH3:24])=[C:11]1[CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 12896473Azane;hydrateHCID 22627246HCID 22627246, compound

Product 1

HCID 22627454HCID 22627454, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution phosphorus oxychloride (0.031 ml) in dimethylformamide (1.2 ml) was added 1-(2-chlorobenzyl)-2-ethyl-3-propionylindole-6-carboxamide (112 mg) at 0° C., and the mixture was stirred for 15 minutes. The resulting mixture was poured into ammonia water and ice, and then extracted with ethyl acetate. The organic phase was washed with brine, dried over sodium sulfate and evaporated in vacuo. The residue was triturated with a mixture of hexane and isopropyl ether to give 1-(2-chlorobenzyl)-2-ethyl-3-propionylindole-6-carbonitrile (93 mg) as a solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated in vacuo
  5. customThe residue was triturated with a mixture of hexane and isopropyl ether

Sources & evidence

ORD record
ord-6ac0235871e04fd49ec6c08e18686953
Source dataset
uspto-grants-2002_03
Patent number
US06358992B1

Reaction notes

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