4-Methoxybenzenesulfonyl chloride → HCID 23471003, compound

HRID 127968Notes

Reaction equation

HRID 127968 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[NH2:13][CH2:14][CH2:15][C:16]1[CH:28]=[CH:27][C:19]([O:20][CH2:21][C:22]([O:24]CC)=[O:23])=[CH:18][CH:17]=1>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:13][CH2:14][CH2:15][C:16]2[CH:17]=[CH:18][C:19]([O:20][CH2:21][C:22]([OH:24])=[O:23])=[CH:27][CH:28]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 11118784HCID 11118784, compound

Product 1

HCID 23471003HCID 23471003, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A mixture of 10.35 g. (50 mMol) 4-methoxybenzenesulphonyl chloride and 50 ml. pyridine is added dropwise at 0°-10° C. in the course of 5 minutes to a solution of 11.2 g. (50 mMol) ethyl 4-(2-aminoethyl)-phenoxyacetate in 125 ml. anhydrous pyridine. The reaction mixture is allowed to warm up to ambient temperature and then kept at 60° C. for 45 minutes. Subsequently, the reaction mixture is evaporated to half its volume in a vacuum, then poured into ice-water and acidified with hydrochloric acid. The precipitated viscous mass is dissolved in toluene and the toluene phase successively extracted with dilute hydrochloric acid, an aqueous solution of sodium bicarbonate and water. After drying over anhydrous calcium chloride, the solution is evaporated in a vacuum and the residue triturated with some diethyl ether, crystallization thereby takes place. The product is filtered off with suction and recrystallized from a very small amount of diethyl ether. There are thus obtained 13.0 g. (66% of theory) ethyl 4-[2-(4-methoxybenzenesulphonylamino)-ethyl]-phenoxyacetate; m.p. 82°-83° C.

Workup

  1. additionA mixture of 10.35 g
  2. customSubsequently, the reaction mixture is evaporated to half its volume in a vacuum
  3. additionpoured into ice-water
  4. dissolutionThe precipitated viscous mass is dissolved in toluene
  5. extractionthe toluene phase successively extracted with dilute hydrochloric acid
  6. dry with materialAfter drying over anhydrous calcium chloride
  7. customthe solution is evaporated in a vacuum
  8. customthe residue triturated with some diethyl ether, crystallization
  9. filtrationThe product is filtered off with suction
  10. customrecrystallized from a very small amount of diethyl ether

Sources & evidence

ORD record
ord-a6f99705f7f24baf96616898dca03d46
Source dataset
uspto-grants-1981_03
Patent number
US04258058

Reaction notes

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