Hydrochloric Acid → HCID 53722307, compound

HRID 127972Notes

Reaction equation

HRID 127972 reaction equation
[H-].[Na+].C1(S(NCCC2C=CC(OCC(OCC)=O)=CC=2)(=O)=O)C=CC=CC=1.CI.Cl.[CH3:31][N:32]([S:48]([C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)(=[O:50])=[O:49])[CH2:33][CH2:34][C:35]1[CH:47]=[CH:46][C:38]([O:39][CH2:40][C:41]([O:43]CC)=[O:42])=[CH:37][CH:36]=1>CN(C)P(=O)(N(C)C)N(C)C.C1(C)C=CC=CC=1>[CH3:31][N:32]([S:48]([C:51]1[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=1)(=[O:49])=[O:50])[CH2:33][CH2:34][C:35]1[CH:36]=[CH:37][C:38]([O:39][CH2:40][C:41]([OH:43])=[O:42])=[CH:46][CH:47]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 23470995HCID 23470995, compoundHCID 53920326HCID 53920326, compound

Product 1

HCID 53722307HCID 53722307, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 12679HexamethylphosphoramideSolvent2×

Procedure

0.6 g. (25 mMol) Sodium hydride (suspension in mineral oil) are added to a mixture of 9.1 g. (25 mMol) ethyl 4-[2-(benzenesulphonylamino)-ethyl]-phenoxyacetate, 50 ml. hexamethylphosphoric acid triamide and 50 ml. anhydrous toluene and the reaction mixture subsequently stirred for 2 hours at 80° C. The reaction mixture is then cooled, mixed with a mixture of 10.6 g. (75 mMol) methyl iodide and 10 ml. hexamethylphosphoric acid triamide, stirred for 15 minutes at 20° C. and then kept for 3 hours at 80° C. After cooling, the reaction mixture is poured on to ice water, adjusted to pH 3 by means of hydrochloric acid and extracted several times with toluene. The toluene phase is evaporated and the evaporation residue chromatographed on silica gel with the use of toluene. There are obtained 3.9 g. (41% of theory) pure ethyl 4-[2-(N-methylbenzenesulphonylamino)-ethyl]-phenoxyacetate in the form of a colorless oil with the refractive index nD20 =1.5440.

Workup

  1. temperatureThe reaction mixture is then cooled
  2. additionmixed with a mixture of 10.6 g
  3. temperatureAfter cooling
  4. extractionextracted several times with toluene
  5. customThe toluene phase is evaporated
  6. customthe evaporation residue chromatographed on silica gel with the use of toluene
  7. customThere are obtained 3.9 g

Sources & evidence

ORD record
ord-d5c1acb785294b8b8a272d00d4ed50a5
Source dataset
uspto-grants-1981_03
Patent number
US04258058

Reaction notes

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