Carbon Tetrachloride → HCID 54218464, compound

HRID 1863087Notes

Reaction equation

HRID 1863087 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:21].O[CH2:26][CH2:27][CH2:28][N:29]([CH3:49])[C:30]([C:32]1[N:33]([CH3:48])[C:34]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[C:35]2[C:40]=1[CH:39]=[CH:38][C:37]([Cl:41])=[CH:36]2)=[O:31]>O1CCOCC1>[Cl:21][CH2:26][CH2:27][CH2:28][N:29]([CH3:49])[C:30]([C:32]1[N:33]([CH3:48])[C:34]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[C:35]2[C:40]=1[CH:39]=[CH:38][C:37]([Cl:41])=[CH:36]2)=[O:31]

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 20393369HCID 20393369, compound

Product 1

HCID 54218464HCID 54218464, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 13.6 g. of triphenylphosphine in 40 ml. of carbon tetrachloride and 24 ml. of dioxane is treated with 14.3 g. of 5-chloro-2-methyl-3-phenylisoindole-1-carboxylic acid (3-hydroxypropyl)methylamide and the mixture is subsequently boiled at reflux for 1 hour. After cooling, the mixture is concentrated to dryness under reduced pressure. The residual oil is chromatographed on 800 g. of silica gel using methylene chloride/ethyl acetate (4:1) for the elution. The homogeneous fractions yield analytically pure 5-chloro-2-methyl-3-phenylisoindole-1-carboxylic acid (3-chloropropyl)methylamide as a thick yellow oil.

Workup

  1. temperatureat reflux for 1 hour
  2. temperatureAfter cooling
  3. concentrationthe mixture is concentrated to dryness under reduced pressure
  4. customThe residual oil is chromatographed on 800 g
  5. washfor the elution

Sources & evidence

ORD record
ord-2508317066fe4edba4a26d8625f6da6a
Source dataset
uspto-grants-1979_09
Patent number
US04167632

Reaction notes

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