Dimethylformamide → HCID 54091384, compound

HRID 1112491Notes

Reaction equation

HRID 1112491 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[N:12]([CH2:19][CH2:20][N:21]([CH2:24][CH3:25])[CH2:22][CH3:23])[C:11](=[O:26])[CH2:10][N:9]=2)=[CH:4][CH:3]=1.CN(C)C=O.[H-].[Na+]>O>[CH2:22]([N:21]([CH2:24][CH3:25])[CH2:20][CH2:19][NH:12][C:11]([C:10]1[NH:9][C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[C:14]2[C:15]=1[CH:16]=[CH:17][CH:18]=[CH:13]2)=[O:26])[CH3:23]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 20393368HCID 20393368, compound

Product 1

HCID 54091384HCID 54091384, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 11.1 g. of 5-(p-chlorophenyl)-1-[2-(diethylamino)ethyl]-1,3-dihydro-2H-1,4-benzodiazepin-2-one in 100 ml. of dimethylformamide is treated under an atmosphere of argon at room temperature with 0.035 mol. of sodium hydride (1.55 g. of a 55% dispersion in mineral oil). The mixture is first warmed to 60° C. over a period of about 30 minutes, then stirred at this temperature for 1 hour and thereafter at 70° C. for 1 hour. After cooling, 4 ml. of water are added dropwise and the mixture is then poured on to 800 ml. of ice-water. After the addition of 30 g. of sodium chloride, the precipitated product is extracted with methylene chloride. The organic phase is washed with a saturated sodium chloride solution, dried over sodium sulfate and concentrated to dryness. The oily residue obtained crystallizes upon trituration with hexane. Recrystallization from ethyl acetate yields 3-(p-chlorophenyl)isoindole-1-carboxylic acid [2-(diethylamino)ethyl]amide in the form of felt-like greenish crystals having a melting point of 145°-147° C.

Workup

  1. waitat 70° C. for 1 hour
  2. temperatureAfter cooling
  3. additionthe mixture is then poured on to 800 ml
  4. additionAfter the addition of 30 g
  5. extractionof sodium chloride, the precipitated product is extracted with methylene chloride
  6. washThe organic phase is washed with a saturated sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated to dryness
  9. customThe oily residue obtained
  10. customcrystallizes upon trituration with hexane
  11. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-290cdce555ae4439a29966793a86d410
Source dataset
uspto-grants-1978_10
Patent number
US04122265

Reaction notes

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