Chloroacetyl chloride → 2-Chloroacetyl-5-nitroisoindoline

HRID 722030Notes

Reaction equation

HRID 722030 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[CH2:9][NH:8][CH2:7]2)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[Cl:19][CH2:20][C:21](Cl)=[O:22]>C(OCC)(=O)C>[Cl:19][CH2:20][C:21]([CH:9]1[C:10]2[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=2)[CH2:7][NH:8]1)=[O:22]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 11430Potassium CarbonateHCID 64244695-Nitroisoindoline

Product 1

HCID 218825782-Chloroacetyl-5-nitroisoindoline

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension in which 42.8 g of 5-nitroisoindoline had been added to an aqueous potassium carbonate solution (108 g of potassium carbonate, 200 ml of water) was added dropwise 200 ml of an ethyl acetate solution containing 31.2 ml of chloroacetyl chloride at 0° C. over 1 hour. The mixture was further stirred at 0° C. for 45 minutes and precipitates were collected by filtration. The obtained solid-was treated with activated carbon in ethyl acetate and recrystallized to obtain 2-chloroacetyl-5-nitroisoindoline.

Workup

  1. customprecipitates
  2. filtrationwere collected by filtration
  3. additionThe obtained solid-was treated with activated carbon in ethyl acetate
  4. customrecrystallized

Sources & evidence

ORD record
ord-16ecc3fb5895401aaa6c94df0a38152c
Source dataset
uspto-grants-2006_11
Patent number
US07138397B2

Reaction notes

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