Water → HCID 20446161, compound

HRID 2418384Notes

Reaction equation

HRID 2418384 reaction equation
[S:1](Cl)([CH3:4])(=[O:3])=[O:2].[NH2:6][C:7]1[C:12]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[Cl:20])=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23].O>N1C=CC=CC=1>[S:1]([NH:6][C:7]1[C:12]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[Cl:20])=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])([CH3:4])(=[O:3])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 20446151HCID 20446151, compound

Product 1

HCID 20446161HCID 20446161, compoundYield 24.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A solution of mesyl chloride (0.95 g) in pyridine (3 ml) was added to a solution of ethyl 2-[2-amino-3-(2-chlorophenoxy)phenyl]acetate (2.3 g) in pyridine (10 ml), and the mixture was stirred for an hour. The reaction mixture was poured into water (100 ml) and extracted with diethyl ether (80 ml×2). The extract was washed with 5% hydrochloric acid (50 ml×2) and saline, dried over magnesium sulfate and then evaporated in vacuo. The oily residue (2.5 g) was crystallized by treating with ethanol and the resultant solid substance was recrystallized from ethanol to give ethyl 2-[2-mesylamino-3-(2-chlorophenoxy)phenyl]acetate (0.7 g). mp 145°-149° C.

Workup

  1. extractionextracted with diethyl ether (80 ml×2)
  2. washThe extract was washed with 5% hydrochloric acid (50 ml×2) and saline
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe oily residue (2.5 g) was crystallized
  6. additionby treating with ethanol
  7. customthe resultant solid substance was recrystallized from ethanol

Sources & evidence

ORD record
ord-ce01b148a6854d1a927f6a3c318bffee
Source dataset
uspto-grants-1984_09
Patent number
US04472433

Reaction notes

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