Hydrochloric Acid → HCID 4252596, compound

HRID 1838217Notes

Reaction equation

HRID 1838217 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][CH:3]=1.[O:9]=[C:10]([CH3:14])[C:11](Cl)=[O:12].Cl>ClCCl.C(N(CC)CC)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:11](=[O:12])[C:10](=[O:9])[CH3:14])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 78124-ChloroanilineHCID 5217912-Oxopropanoyl chloride

Product 1

HCID 4252596HCID 4252596, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent3×HCID 8471TriethylamineSolvent

Conditions

Temperature
-60 °C

Procedure

26.3 g of 4-chlorophenylamine in 150 ml of dichloromethane and 35 ml of triethylamine are added, at −60° C., to 22 g of 2-oxopropionyl chloride (prepared according to Synthesis, 1975, 163-164 from 2-oxopropionic acid and 1,1-dichlorodimethyl ether) in 350 ml of dichloromethane. The reaction mixture is stirred at −60° C. for 2 hours and then 200 ml of a 0.15N aqueous hydrochloric acid solution and 500 ml of dichloromethane are added at −30° C. The organic phase is extracted, washed with a 0.25N aqueous hydrochloric acid solution and dried over sodium sulphate. The solvents are evaporated under reduced pressure and the residue obtained is crystallized from dichloromethane;

Workup

  1. extractionThe organic phase is extracted
  2. washwashed with a 0.25N aqueous hydrochloric acid solution
  3. dry with materialdried over sodium sulphate
  4. customThe solvents are evaporated under reduced pressure
  5. customthe residue obtained
  6. customis crystallized from dichloromethane

Sources & evidence

ORD record
ord-e665b7dfb5434b6596ef75489748249a
Source dataset
uspto-grants-2004_01
Patent number
US06673790B1

Reaction notes

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