Dimethylformamide → HCID 13851149, compound

HRID 543393Notes

Reaction equation

HRID 543393 reaction equation
[Cl:1][C:2]1[C:15]2[O:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:16])[C:6]=2[CH:5]=[CH:4][C:3]=1[OH:17].C(=O)([O-])[O-].[K+].[K+].Br[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27].CN(C=O)C>O>[Cl:1][C:2]1[C:15]2[O:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:16])[C:6]=2[CH:5]=[CH:4][C:3]=1[O:17][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 15617000HCID 15617000, compound

Product 1

HCID 13851149HCID 13851149, compoundYield 67.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.2 g of 4-chloro-3-hydroxy-9-oxo-9H-xanthene, 1.7 g of potassium carbonate, 2.1 g of ethyl bromoacetate and 30 ml of DMF was stirred at 60°-70° C. for 3 hours. After cooling the mixture, water was added and the resulting crystal was recovered by filtration, washed with water and dried. Recrystallization from ethanol gave 1.1 g of ethyl 4-chloro-9-oxo-9H-xanthene-3-yloxyacetate. m.p. 183°-185° C.

Workup

  1. additionwas added
  2. filtrationthe resulting crystal was recovered by filtration
  3. washwashed with water
  4. customdried
  5. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-0747d5ee95e84eee9d9ad7b3c0514dcc
Source dataset
uspto-grants-1987_04
Patent number
US04661607

Reaction notes

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