Dimethylcarbamoyl Chloride → HCID 131715535, compound

HRID 1252710Notes

Reaction equation

HRID 1252710 reaction equation
[Cl:1][C:2]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH:9]=[C:8]2[C:3]=1[CH2:4][C:5](=[O:23])[NH:6][CH:7]2[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[Cl:22].[CH3:24][N:25]([CH3:29])[C:26]([Cl:28])=O>>[OH2:23].[ClH:1].[Cl:1][C:2]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH:9]=[C:8]2[C:3]=1[CH2:4][C:5]([N:25]([CH3:26])[CH3:24])=[N:6][CH:7]2[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[Cl:22].[Cl:1][C:2]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH:9]=[C:8]2[C:3]=1[CH2:4][C:26]([N:25]([CH3:29])[CH3:24])=[N:6][CH:7]2[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[Cl:22].[ClH:28]

Participants

3

Reactant 2

HCID 6598Dimethylcarbamoyl ChlorideHCID 20138985HCID 20138985, compound

Product 1

HCID 131715535HCID 131715535, compound

Procedure

5-Chloro-1-(2'-chlorophenyl)-1,4-dihydro-benz[g]isoquinol-3-one (Description 3) (4.5 g) was dissolved in dimethylcarbamyl chloride (25 ml) on an oil bath (bath temperature 160°-170° C. ) for 2 h. The mixture was cooled, evaporated under reduced pressure and partitioned between water (50 ml), 5M hydrochloric acid, ethyl acetate (25 ml) and chloroform (25 ml). The organic layer was separated and extracted with water (25 ml). The combined aqueous extracts were washed with ethyl acetate (2×25 ml) and basified with 10% sodium hydroxide solution. The oil so formed was extracted with ethyl acetate (2×100 ml) and the combined organic extracts dried over sodium sulphate. The solution was filtered and reduced to 100 ml under reduced pressure. Ethereal hydrogen chloride was added to precipitate the salt to give 5-Chloro-1-(2'-chlorophenyl)-3-dimethylamino-1,4-dihydro-benz[g]isoquinoline hydrochloride hemihydrate (0.85 g) m.p. 232°-234° C.

Workup

  1. temperatureThe mixture was cooled
  2. customevaporated under reduced pressure
  3. custompartitioned between water (50 ml), 5M hydrochloric acid, ethyl acetate (25 ml) and chloroform (25 ml)
  4. customThe organic layer was separated
  5. extractionextracted with water (25 ml)
  6. washThe combined aqueous extracts were washed with ethyl acetate (2×25 ml)
  7. customThe oil so formed
  8. extractionwas extracted with ethyl acetate (2×100 ml)
  9. dry with materialthe combined organic extracts dried over sodium sulphate
  10. filtrationThe solution was filtered
  11. additionEthereal hydrogen chloride was added
  12. customto precipitate the salt

Sources & evidence

ORD record
ord-e82c27cbdb79416f9b81ab5b1221fd4a
Source dataset
uspto-grants-1988_05
Patent number
US04745115

Reaction notes

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