Triethylamine → methyl 2-[N-(4-chlorophenylmethyl)-ethoxycarbonylmethylsulfonylamino]-phenylacetate

HRID 1381512Notes

Reaction equation

HRID 1381512 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH2:16][C:17]([O:19][CH3:20])=[O:18])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH2:28]([O:30][C:31]([CH2:33][S:34](Cl)(=[O:36])=[O:35])=[O:32])[CH3:29]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][N:9]([S:34]([CH2:33][C:31]([O:30][CH2:28][CH3:29])=[O:32])(=[O:36])=[O:35])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH2:16][C:17]([O:19][CH3:20])=[O:18])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12225100Ethyl (chlorosulfonyl)acetateHCID 54137648Methyl 2-(4-chlorophenylmethylamino)-phenylacetate

Product 1

HCID 70394946methyl 2-[N-(4-chlorophenylmethyl)-ethoxycarbonylmethylsulfonylamino]-phenylacetateYield 54.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a stirred solution of 48 g of methyl 2-(4-chlorophenylmethylamino)-phenylacetate in 1.2 l of toluene containing 26 ml of triethylamine is added 31 g of ethoxycarbonylmethylsulfonyl chloride in 50 ml of toluene in a dropwise manner over a period of 15 minutes maintaining the temperature of the reaction below 10°. The reaction mixture is then allowed to stir overnight at room temperature and poured into 2 1 of ice-water and the organic layer separated. The toluene extracts are washed with 3×750 ml brine, separated, dried over anhydrous magnesium sulfate, filtered and the solvent evaporated under reduced pressure to yield 40 g of methyl 2-[N-(4-chlorophenylmethyl)-ethoxycarbonylmethylsulfonylamino]-phenylacetate which may be crystallized from ether-hexane (4:1); m.p. 86°-88°.

Workup

  1. temperaturemaintaining
  2. customthe temperature of the reaction below 10°
  3. customthe organic layer separated
  4. washThe toluene extracts are washed with 3×750 ml brine
  5. customseparated
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-56791ba47455451c8c5278d10f23bafd
Source dataset
uspto-grants-1989_02
Patent number
US04803197

Reaction notes

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