Ethanol → HCID 19974050, compound

HRID 1451268Notes

Reaction equation

HRID 1451268 reaction equation
Cl.[CH3:2][NH:3][CH3:4].C([N:7]([CH2:10][CH3:11])[CH2:8][CH3:9])C.ClCC(C1C=[CH:20][C:19]([C:22]2[C:28]3[CH:29]=[C:30]4[O:35][CH2:34][O:33][C:31]4=[CH:32][C:27]=3[CH2:26][C:25]([CH3:36])=[N:24][N:23]=2)=[C:18](N)[CH:17]=1)=O.C([OH:40])C>>[CH3:2][N:3]([CH3:4])[CH2:11][C:10]([NH:7][C:8]1[CH:9]=[CH:20][C:19]([C:22]2[C:28]3[CH:29]=[C:30]4[O:35][CH2:34][O:33][C:31]4=[CH:32][C:27]=3[CH2:26][C:25]([CH3:36])=[N:24][N:23]=2)=[CH:18][CH:17]=1)=[O:40]

Participants

5

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 86749043HCID 86749043, compound

Product 1

HCID 19974050HCID 19974050, compound

Procedure

After adding 0.66 g (8.12 mmol) of dimethylamine hydrochloride and 1.86 ml (13.4 mmol) of triethylamine to a suspension of 1.5 g (4.06 mmol) of 1-(4-chloroacetyl-amino-phenyl)-4-methyl-7,8-methylenedioxy-5H-2,3-benzodiazepine in 60 ml of ethanol, the reaction mixture was refluxed for 8 hours, then evaporated. The residue was dissolved in 30 ml of dichloromethane, washed with 20 ml of 4% NaOH solution, then 2×20 ml of distilled water, dried and evaporated under reduced pressure. After treating with water, the crystalline residue was filtered to give 1.27 g of raw product, m.p. 211°-213° C. After recrystallization from 10 ml of ethanol 1.1 g (71.4%) of aimed product were obtained, m.p.: 213°-215° C.

Workup

  1. temperaturethe reaction mixture was refluxed for 8 hours
  2. customevaporated
  3. dissolutionThe residue was dissolved in 30 ml of dichloromethane
  4. washwashed with 20 ml of 4% NaOH solution
  5. dry with material2×20 ml of distilled water, dried
  6. customevaporated under reduced pressure
  7. additionAfter treating with water
  8. filtrationthe crystalline residue was filtered

Sources & evidence

ORD record
ord-9dc1d85d67974407a30e5258d82b7352
Source dataset
uspto-grants-1997_02
Patent number
US05604223

Reaction notes

Loading…