Hydrochloric Acid → HCID 68141253, compound

HRID 1605486Notes

Reaction equation

HRID 1605486 reaction equation
[CH3:1][NH:2][CH2:3][C:4]([NH:6][C:7]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:8]=1[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:10])=[O:5].[C:22](#[N:25])[CH:23]=[CH2:24].Cl>C(OCC)C>[ClH:21].[C:22]([CH2:23][CH2:24][N:2]([CH3:1])[CH2:3][C:4]([NH:6][C:7]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:8]=1[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:10])=[O:5])#[N:25]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7855Acrylonitrile2×HCID 215694492-(Methylamino-acetamido)-5-chloro-benzophenone

Product 1

HCID 68141253HCID 68141253, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

3.0 g of 2-(methylamino-acetamido)-5-chloro-benzophenone were dissolved in 30 mls. of anhydrous alcohol and then mixed with 2.0 g of freshly distilled acrylonitrile. The mixture was stirred for 2 hours at room temperature and then heated under reflux for a further 8 hours. After being allowed to stand overnight at room temperature a further 2.0 g of freshly distilled acrylonitrile was added and the mixture heated under reflux with stirring for a further 4 hours. At this point a sample showed in a thin-layer chromatogram a uniform point which differed from that of the initial product. The turbid solution was filtered and concentrated in vacuo (approx. 0.1 mm Hg), 3.0 g of a colourless oil being obtained. This residue was dissolved in anhydrous diethyl ether. After passing dry hydrogen chloride into this solution, 3.6 g of 2-(5-cyano-3-methyl-3-aza-pentanamido)-5-chloro-benzophenone hydrochloride were obtained, corresponding to 92% of theory. The product had a melting point of 166°-168°. The RF value in a thin-layer chromatogram in methanol as flow medium was 0.85.

Workup

  1. temperatureheated
  2. temperatureunder reflux for a further 8 hours
  3. waitto stand overnight at room temperature
  4. temperaturethe mixture heated
  5. temperatureunder reflux
  6. stirringwith stirring for a further 4 hours
  7. filtrationThe turbid solution was filtered
  8. concentrationconcentrated in vacuo (approx. 0.1 mm Hg), 3.0 g of a colourless oil
  9. custombeing obtained

Sources & evidence

ORD record
ord-7bf73ee821fa40d396f3f3b14d2ab70a
Source dataset
uspto-grants-1976_04
Patent number
US03950383

Reaction notes

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