Chloroacetyl chloride → 2-Chloro-1-[4-(4-nitrophenyl)[1,4]diazepan-1-yl]ethanone

HRID 8551Notes

Reaction equation

HRID 8551 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:16][CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[Cl:23][CH2:24][C:25](Cl)=[O:26]>CN(C)C=O>[Cl:23][CH2:24][C:25]([N:13]1[CH2:14][CH2:15][CH2:16][N:10]([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)[CH2:11][CH2:12]1)=[O:26]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 11430Potassium CarbonateHCID 50559501-(4-Nitrophenyl)-1,4-diazepane

Product 1

HCID 219828292-Chloro-1-[4-(4-nitrophenyl)[1,4]diazepan-1-yl]ethanoneYield 75.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

22.1 g (0.1 mol) of 1-(4-nitrophenyl)[1,4]diazepane, 8.3 g (0.06 mol) of potassium carbonate and 120 ml of dimethylformamide were mixed together in a reactor. 8.3 ml (0.11 mol) of chloroacetyl chloride were added to this stirred suspension, while maintaining the temperature between 15 and 25° C. After stirring for about ten hours at room temperature, 400 g of slightly hydrochloric ice-cold water were added to the mixture: a yellow gum crystallized. After filtering off by suction, washing with water and drying under vacuum over phosphorus pentoxide, 22.4 g of yellow crystals were obtained (yield=75%).

Workup

  1. temperaturewhile maintaining the temperature between 15 and 25° C
  2. addition400 g of slightly hydrochloric ice-cold water were added to the mixture
  3. customa yellow gum crystallized
  4. filtrationAfter filtering off by suction
  5. washwashing with water
  6. dry with materialdrying under vacuum over phosphorus pentoxide

Sources & evidence

ORD record
ord-3c966fe269e1451a867618710487421e
Source dataset
uspto-grants-2006_08
Patent number
US07090703B2

Reaction notes

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