Chloroacetyl chloride → HCID 13375745, compound

HRID 745862Notes

Reaction equation

HRID 745862 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[NH2:6][C:7]1[CH:16]=[C:15]2[C:10]([C:11](=[O:30])[C:12]([CH2:27][CH2:28][CH3:29])=[C:13]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([O:25][CH3:26])=[O:24])=[CH:19][CH:18]=3)[O:14]2)=[CH:9][CH:8]=1.C([O-])([O-])=O.[K+].[K+]>C1C=CC=CC=1>[Cl:1][CH2:2][C:3]([NH:6][C:7]1[CH:16]=[C:15]2[C:10]([C:11](=[O:30])[C:12]([CH2:27][CH2:28][CH3:29])=[C:13]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([O:25][CH3:26])=[O:24])=[CH:19][CH:18]=3)[O:14]2)=[CH:9][CH:8]=1)=[O:4]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 11430Potassium CarbonateHCID 23312583HCID 23312583, compound

Product 1

HCID 13375745HCID 13375745, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

8 cc of chloroacetyl chloride are added, with stirring, to a mixture consisting of 9.5 g of methyl 7-amino-3-propyl-4'-flavonecarboxylate made according to Example 7a, 1 liter of benzene and 9 g of anhydrous K2CO3. The mixture is heated to reflux of the benzene for 2 hours, then cooled. The benzene phase is washed with water. A precipitate is formed which is filtered and dissolved in chloroform. The benzene and chloroform phases are evaporated. Methyl 7-(2-chloracetamido)-3-propyl-4'-flavonecarboxylate is obtained with a yield of 80%. MP=162° C.

Workup

  1. temperatureThe mixture is heated
  2. temperaturecooled
  3. washThe benzene phase is washed with water
  4. customA precipitate is formed which
  5. filtrationis filtered
  6. dissolutiondissolved in chloroform
  7. customThe benzene and chloroform phases are evaporated

Sources & evidence

ORD record
ord-34430014ea38450da89e52d6d3a9ae47
Source dataset
uspto-grants-1986_07
Patent number
US04600788

Reaction notes

Loading…