Water → HCID 13392295, compound

HRID 235887Notes

Reaction equation

HRID 235887 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([C:17]3[O:18][CH:19]=[CH:20][CH:21]=3)=[C:11]([CH2:13][C:14]([OH:16])=[O:15])[N:12]=2)=[CH:4][CH:3]=1.[CH2:22](Br)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].C(N(CC)CC)C.O>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([C:17]3[O:18][CH:19]=[CH:20][CH:21]=3)=[C:11]([CH2:13][C:14]([O:16][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[O:15])[N:12]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 123691-BromoheptaneHCID 13392284HCID 13392284, compound

Product 1

HCID 13392295HCID 13392295, compoundYield 42.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.5 g of 2-[2-(4-chlorophenyl)-5-(2-furyl)-4-oxazolyl]acetic acid and 1.0 g of n-heptyl bromide in 25 ml of dimethylformamide is dropwise added 0.92 g of triethylamine at room temperature. The mixture is stirred at 30° to 40° C. for 4 hours. Then, the mixture is poured into water, and the aqueous mixture is extracted with a mixture of diethyl ether and ethyl acetate (1:1). The extract is treated in the same manner as described in Example 27, whereby 0.85 g of n-heptyl 2-[2-(4-chlorophenyl)-5-(2-furyl)-4-oxazolyl]acetate is obtained. Yield: 42.7%

Workup

  1. customat room temperature
  2. extractionthe aqueous mixture is extracted with a mixture of diethyl ether and ethyl acetate (1:1)
  3. additionThe extract is treated in the same manner

Sources & evidence

ORD record
ord-493417e909bd44f3bfd832dc6dd3b3b2
Source dataset
uspto-grants-1987_02
Patent number
US04642313

Reaction notes

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