P-Toluenesulfonamide → HCID 14479963, compound

HRID 1761677Notes

Reaction equation

HRID 1761677 reaction equation
[C:1]1([C:7]2[S:8][CH:9]=[C:10]([CH2:12][O:13][C:14]3[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=3)[C:17]([OH:19])=O)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:35][C:36]1[CH:37]=[CH:38][C:39]([S:42]([NH2:45])(=[O:44])=[O:43])=[CH:40][CH:41]=1>C1(C)C=CC=CC=1.C(Cl)Cl>[CH3:35][C:36]1[CH:37]=[CH:38][C:39]([S:42]([NH:45][C:17](=[O:19])[C:16]2[CH:20]=[CH:21][CH:22]=[C:14]([O:13][CH2:12][C:10]3[N:11]=[C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[S:8][CH:9]=3)[CH:15]=2)(=[O:44])=[O:43])=[CH:40][CH:41]=1

Participants

6

Reactant 3

HCID 6269P-ToluenesulfonamideHCID 682631,1'-CarbonyldiimidazoleHCID 14479962HCID 14479962, compound

Product 1

HCID 14479963HCID 14479963, compoundYield 18.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5.48 g (0.0176 mol) of 3-[(2-phenyl-4-thiazolyl)methoxy]benzoic acid in 100 ml of toluene are added 3.24 g (0.0200 mol) of 1,1'-carbonyldiimidazole and the solution is stirred for 1 hour. To this solution, 3.01 g (0.0176 mol) p-toluenesulfonamide are added and the solution is refluxed for 16 hours. After cooling, the bottom layer is isolated and concentrated in vacuo to obtain a clear oil. The clear oil is dissolved in methylene chloride and is washed twice with pH 4 buffer solution, twice with water and is concentrated in vacuo to obtain a residue. Recrystallization from toluene/ethyl acetate gives 1.5 g (18%) of crystals, m.p. 170°-172° C.

Workup

  1. temperaturethe solution is refluxed for 16 hours
  2. temperatureAfter cooling
  3. customthe bottom layer is isolated
  4. concentrationconcentrated in vacuo
  5. customto obtain a clear oil
  6. washis washed twice with pH 4 buffer solution, twice with water
  7. concentrationis concentrated in vacuo
  8. customto obtain a residue
  9. customRecrystallization from toluene/ethyl acetate

Sources & evidence

ORD record
ord-69a44fb8023f485fb4b1c2a944641610
Source dataset
uspto-grants-1989_05
Patent number
US04826990

Reaction notes

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