N,N-Dimethylaniline → HCID 53924313, compound

HRID 1902216Notes

Reaction equation

HRID 1902216 reaction equation
CN(C)C1C=CC=CC=1.[C:10]([CH:12]=[C:13]1[C:19]2=[CH:20][S:21][CH:22]=[C:18]2[C:17](=O)[NH:16][C:15]2=[CH:24][S:25][CH:26]=[C:14]12)#[N:11].P(Cl)(Cl)([Cl:29])=O>>[Cl:29][C:17]1[C:18]2[C:19](=[CH:20][S:21][CH:22]=2)[C:13](=[CH:12][C:10]#[N:11])[C:14]2[C:15](=[CH:24][S:25][CH:26]=2)[N:16]=1

Participants

4

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 54210848HCID 54210848, compound

Product 1

HCID 53924313HCID 53924313, compoundYield 96%

Procedure

140 ml of phosphorus oxychloride and 1.5 ml of N,N-dimethylaniline are added to 14.0 g (54 mmoles) of 9-cyanomethylene-4,5-dihydro-dithieno[3,4-b:4',3'-e]azepin-5-one (cis/trans-isomer mixture) and the mixture is refluxed under nitrogen for 1 hour. After all the excess phosphorus oxychloride and dimethylaniline have been distilled off under reduced pressure from an oil pump, the residue is partitioned between methylene chloride and water, the aqueous phase is extracted twice more with methylene chloride and the combined organic phases are washed thoroughly with dilute HCl and water. Drying and concentrating the organic phase gives 14.4 g (96%) of 5-chloro-9-cyanomethylene-dithieno[3,4-b:4',3'-e]azepine, which is sufficiently pure for the further reaction.

Workup

  1. temperaturethe mixture is refluxed under nitrogen for 1 hour
  2. distillationAfter all the excess phosphorus oxychloride and dimethylaniline have been distilled off under reduced pressure from an oil pump
  3. customthe residue is partitioned between methylene chloride and water
  4. extractionthe aqueous phase is extracted twice more with methylene chloride
  5. washthe combined organic phases are washed thoroughly with dilute HCl and water
  6. customDrying
  7. concentrationconcentrating the organic phase

Sources & evidence

ORD record
ord-b4744fb8cbe04da8b45d04a1621c2be5
Source dataset
uspto-grants-1982_12
Patent number
US04362727

Reaction notes

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