Dimethylformamide → HCID 13290033, compound

HRID 652653Notes

Reaction equation

HRID 652653 reaction equation
[Cl:1][C:2]1[C:3]([OH:17])=[CH:4][C:5]2[CH:9]=[C:8]([CH:10]3[CH2:14][CH2:13][CH2:12][CH2:11]3)[S:7][C:6]=2[C:15]=1[Cl:16].Br[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>CC(=O)CC.O>[Cl:1][C:2]1[C:3]([O:17][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:4][C:5]2[CH:9]=[C:8]([CH:10]3[CH2:11][CH2:12][CH2:13][CH2:14]3)[S:7][C:6]=2[C:15]=1[Cl:16]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 13290032HCID 13290032, compound

Product 1

HCID 13290033HCID 13290033, compoundYield 76.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 9.0 g of 6,7-dichloro-2-cyclopentyl-5-hydroxybenzo[b]thiophene, 6.35 g of ethyl bromoacetate, 4.0 g of potassium carbonate and 10 ml of dimethylformamide in 200 ml of 2-butanone is refluxed for 16 hours. The cooled mixture is diluted with water (200 ml), extracted with 3×300 ml-portions of dichloromethane, and the combined organic solution is dried over anhydrous magnesium sulfate. Removal of solvents leave a colorless oil which crystallizes on cooling to give 8.9 g of ethyl [(6,7-dichloro-2-cyclopentylbenzo[b]thien-5-yl)oxy]acetate or prisms, mp 65°-67°.

Workup

  1. temperatureis refluxed for 16 hours
  2. extractionextracted with 3×300 ml-portions of dichloromethane
  3. dry with materialthe combined organic solution is dried over anhydrous magnesium sulfate
  4. customRemoval of solvents
  5. customleave a colorless oil which
  6. customcrystallizes
  7. temperatureon cooling

Sources & evidence

ORD record
ord-4e1664bf7ab7405d9e9b31c65303c4f1
Source dataset
uspto-grants-1987_06
Patent number
US04672138

Reaction notes

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