Water → HCID 14620887, compound

HRID 1709266Notes

Reaction equation

HRID 1709266 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][C:5]1[CH:16]=[CH:15][C:8]([O:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[C:7]([F:17])[CH:6]=1.C(=O)([O-])[O-].[K+].[K+].O.[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1>C(OCC)(=O)C>[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([S:32]([NH:2][CH2:3][CH2:4][C:5]2[CH:16]=[CH:15][C:8]([O:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[C:7]([F:17])[CH:6]=2)(=[O:34])=[O:33])=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 962WaterHCID 73984-Chlorobenzenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 14620884HCID 14620884, compound

Product 1

HCID 14620887HCID 14620887, compoundYield 93.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

1 g of methyl 4-(2-aminoethyl)-2-fluorophenoxyacetate hydrochloride is added to a mixture of 30 ml of ethyl acetate, 1.58 g of potassium carbonate and 15 ml of water, and a solution of 0.78 g of 4-chlorophenylsulfonyl chloride in 15 ml of ethyl acetate is added dropwise thereto at room temperature. After the mixture is stirred for 2 hours, the ethyl acetate layer is separated therefrom, washed, dried and evaporated to remove the solvent. The residue is recrystallized from a mixture of ethyl acetate, isopropylether and n-hexane. 1.39 g of methyl 4-[2-(4-chlorophenyl)sulfonylaminoethyl]-2-fluorophenoxyacetate are obtained as colorless prisms.

Workup

  1. customat room temperature
  2. customthe ethyl acetate layer is separated
  3. washwashed
  4. customdried
  5. customevaporated
  6. customto remove the solvent
  7. customThe residue is recrystallized from a mixture of ethyl acetate, isopropylether and n-hexane

Sources & evidence

ORD record
ord-ea2a3a5b7c8d4792aefdddb0e81ce57b
Source dataset
uspto-grants-1990_08
Patent number
US04948810

Reaction notes

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