Hydrochloric Acid → 2-Acetyl-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]benzenesulfonamide

HRID 1164177Notes

Reaction equation

HRID 1164177 reaction equation
[CH3:1][Li].[CH3:3][O:4][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[N:8]=[C:7]([NH:13][C:14]([NH:16][S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:26](O)=[O:27])(=[O:19])=[O:18])=[O:15])[N:6]=1.Cl>CCOCC.O1CCCC1>[CH3:12][O:11][C:9]1[CH:10]=[C:5]([O:4][CH3:3])[N:6]=[C:7]([NH:13][C:14]([NH:16][S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:26](=[O:27])[CH3:1])(=[O:19])=[O:18])=[O:15])[N:8]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 13097297N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-2-carboxybenzenesulfonamideHCID 178418348HCID 178418348, compound

Product 1

HCID 130972992-Acetyl-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A methyllithium solution in ether (1.4 M, 40 ml) was added to a solution of 1.0 g of N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-carboxybenzenesulfonamide in 50 ml of dry tetrahydrofuran at room temperature. The resulting yellow slurry was stirred for 4 hours and the dilute hydrochloric acid was added. The mixture was then extracted with methylene chloride. The organic extracts were washed, dried, and evaporated in vacuo to dryness. The crude product was purified by preparative TLC, eluted with ethyl acetate/hexane (1:1), m.p. 126°-128° C.

Workup

  1. extractionThe mixture was then extracted with methylene chloride
  2. washThe organic extracts were washed
  3. customdried
  4. customevaporated in vacuo to dryness
  5. customThe crude product was purified by preparative TLC
  6. washeluted with ethyl acetate/hexane (1:1), m.p. 126°-128° C.

Sources & evidence

ORD record
ord-b334f2afc72242019d7ccd94a95671d5
Source dataset
uspto-grants-1983_01
Patent number
US04368069

Reaction notes

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