Ammonia → 3-[2-(4-Chlorobenzenesulphonamido)-ethyl]-phenoxyacetic acid amide

HRID 2248143Notes

Reaction equation

HRID 2248143 reaction equation
N1C([NH:6][C:7](=[O:29])[CH2:8][O:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][CH2:17][NH:18][S:19]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)(=[O:21])=[O:20])[CH:11]=2)=NN=N1.C1(N=C=NC2CCCCC2)CCCCC1.N>O1CCCC1>[Cl:28][C:25]1[CH:24]=[CH:23][C:22]([S:19]([NH:18][CH2:17][CH2:16][C:12]2[CH:11]=[C:10]([CH:15]=[CH:14][CH:13]=2)[O:9][CH2:8][C:7]([NH2:6])=[O:29])(=[O:20])=[O:21])=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 10868DicyclohexylcarbodiimideHCID 178521404HCID 178521404, compound

Product 1

HCID 193881183-[2-(4-Chlorobenzenesulphonamido)-ethyl]-phenoxyacetic acid amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 29.7 g. (72 mMol) 3-[2-(4-chlorobenzenesulphonamido)-ethyl]-phenoxymalonic acid (preparation see Example 10 e)) in 150 ml. anhydrous tetrahydrofuran are added 14.8 g. (72 mMol) dicyclohexylcarbodiimide. The reaction mixture is stirred for 10 minutes and then a weak current of ammonia is passed in for about 1 hour. It is then left to stand for 2 hours and filtered. The mother liquor is evaporated and the residue recrystallised from isohexane. There are obtained 18.0 g. (68% of theory) of colourless crystals; m.p. 113° C.

Workup

  1. customis passed in for about 1 hour
  2. waitIt is then left
  3. waitto stand for 2 hours
  4. filtrationfiltered
  5. customThe mother liquor is evaporated
  6. customthe residue recrystallised from isohexane
  7. customThere are obtained 18.0 g

Sources & evidence

ORD record
ord-58d463d400d74f03a6d057fdbbfaceec
Source dataset
uspto-grants-1991_08
Patent number
US05037990

Reaction notes

Loading…