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

HRID 235566
Notes
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Reaction equation

HRID 235566 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 EtherSolvent
HCID 8028
Tetrahydrofuran
Solvent

Procedure

A methyllithium solution in ether (1.4M, 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-7f4a46a0dc3d466aa3d5164f88bb48cc
Source dataset
uspto-grants-1987_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04640704

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes