3-Chloropropionyl chloride → HCID 21465211, compound

HRID 1939943Notes

Reaction equation

HRID 1939943 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][CH2:6][CH2:7][C:8](Cl)=[O:9].[Cl:11][C:12]1[CH:13]=[CH:14][C:15]2[NH:19][C:18](=[O:20])[NH:17][C:16]=2[CH:21]=1>CN(C=O)C>[Cl:5][CH2:6][CH2:7][C:8]([C:13]1[C:12]([Cl:11])=[CH:21][C:16]2[NH:17][C:18](=[O:20])[NH:19][C:15]=2[CH:14]=1)=[O:9]

Participants

5

Reactant 3

HCID 693643-Chloropropionyl chlorideHCID 2231315-Chloro-1,3-dihydro-2H-benzimidazol-2-oneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 21465211HCID 21465211, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

44.68 g of aluminium chloride (0.335 mol) are initially introduced into a reaction flask. 4.9 ml of DMF are slowly added dropwise with stirring, the temperature rising to approximately 56° C. 6.9 ml of 3-chloropropionyl chloride (0.072 mol) are added to this mixture. 8.07 g of 6-chloro-2,3-dihydrobenzimidazol-2-one (0.048 mol) are then slowly added in portions and the mixture is stirred at 80° C. for one hour. After completion of the reaction the reaction mixture obtained is stirred into 400 g of ice, and the precipitate is filtered off with suction and washed with plenty of water and small amounts of acetone. The reaction leads to a slightly more non-polar product which can be separated by thin-layer chromatography using an eluent consisting of-chloroform and methanol in the mixture ratio 9:1. Yield: 9.72 g of 5-(3-chloro-1-oxopropyl)-6-chloro-2,3-dihydrobenzimidazol-2-one (78.2% of theory); m.p.: 201°-204° C.

Workup

  1. customrising to approximately 56° C
  2. stirringthe mixture is stirred at 80° C. for one hour
  3. customAfter completion of the reaction the reaction mixture
  4. customobtained
  5. filtrationthe precipitate is filtered off with suction
  6. washwashed with plenty of water and small amounts of acetone
  7. customcan be separated by thin-layer chromatography

Sources & evidence

ORD record
ord-9eb418308b5443d08acbb083811b798f
Source dataset
uspto-grants-1997_12
Patent number
US05698553

Reaction notes

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