4-tert-Butylbenzenesulfonamide → HCID 19095805, compound

HRID 486650Notes

Reaction equation

HRID 486650 reaction equation
Cl[C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][CH3:16])=[C:6]([Cl:17])[N:5]=[C:4]([C:18]2[S:19][CH:20]=[CH:21][CH:22]=2)[N:3]=1.[C:23]([C:27]1[CH:32]=[CH:31][C:30]([S:33]([NH2:36])(=[O:35])=[O:34])=[CH:29][CH:28]=1)([CH3:26])([CH3:25])[CH3:24]>CS(C)=O>[C:23]([C:27]1[CH:32]=[CH:31][C:30]([S:33]([NH:36][C:2]2[C:7]([O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[O:15][CH3:16])=[C:6]([Cl:17])[N:5]=[C:4]([C:18]3[S:19][CH:20]=[CH:21][CH:22]=3)[N:3]=2)(=[O:34])=[O:35])=[CH:29][CH:28]=1)([CH3:26])([CH3:24])[CH3:25]

Participants

4

Reactant 2

HCID 2228724-tert-ButylbenzenesulfonamideHCID 19095786HCID 19095786, compound

Product 1

HCID 19095805HCID 19095805, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 0.353 g of 4,6-dichloro-5-(2-methoxyphenoxy)-2-(thiophen-2-yl)-pyrimidine in 5 ml of DMSO was heated to 150° C. with 0.376 g of p-tert-butylbenzenesulphonamide for 30 minutes. The solution was concentrated in a high vacuum and the oily residue was poured on to ice, made acid (pH=3) and the suspension was extracted with ethyl acetate. The organic extracts were combined, washed with water, dried over sodium sulfate and concentrated under reduced pressure. The residue was chromatographed on silica gel with toluene-ethyl acetate 9:1 and yielded 4-tert-butyl-N-[6-chloro-5-(2-methoxyphenoxy)-2-(thiophen-2-yl)-pyrimidin-4-yl]-benzenesulphonamide as a white foam.

Workup

  1. concentrationThe solution was concentrated in a high vacuum
  2. additionthe oily residue was poured on to ice
  3. extractionthe suspension was extracted with ethyl acetate
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was chromatographed on silica gel with toluene-ethyl acetate 9:1

Sources & evidence

ORD record
ord-90eb69fc4acb4edca6c9145ec56f7e3e
Source dataset
uspto-grants-1994_03
Patent number
US05292740

Reaction notes

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