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

HRID 2412380Notes

Reaction equation

HRID 2412380 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([NH:11][C:12]([NH:14][S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[C:24]([OH:26])=O)(=[O:17])=[O:16])=[O:13])[N:4]=1.[CH3:27][Li].O.Cl>O1CCCC1.CCOCC>[C:24]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[S:15]([NH:14][C:12]([NH:11][C:5]1[N:4]=[C:3]([O:2][CH3:1])[CH:8]=[C:7]([O:9][CH3:10])[N:6]=1)=[O:13])(=[O:17])=[O:16])(=[O:26])[CH3:27]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 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 mixture containing 0.85 g of N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-carboxybenzenesulfonamide in 50 ml of anhydrous tetrahydrofuran was treated with 40 ml of a 1.4 molar solution of methyl lithium (low halide, Aldrich) in ether at 25° under a nitrogen atmosphere. The mixture was stirred for 4 hours at 25° and was then poured into 500 ml of water containing 10 ml of concentrated hydrochloric acid. The precipitated oil was extracted into methylene chloride and the oil on evaporation of solvent was purified by preparative thin layer chromatography on silica gel (Analtec, 2000 micron, 20×20 plates) by elution with ethyl acetate/hexane in a one to one ratio. The isolated product was recrystallized from a 1-chlorobutane and hexane mixture to give 0.1 g, m.p. 126°-8°. The infrared absorption showed a broadened carbonyl peak at 1710 cm-1, and the absence of the 3500 and 3400 cm-1 peaks of the starting material. The nuclear magnetic resonance spectrum showed peaks at 2.6 ppm, s, 3H, ##STR60## 4.0 ppm, s, 6H, CH3O of pyrimidine; 5.7 ppm, s, 1H, pyrimidine proton at position 5; and 7.3-7.7 ppm and 8.0 ppm, m, 4H, aromatic, which are consistent with the desired structure.

Workup

  1. extractionThe precipitated oil was extracted into methylene chloride
  2. customthe oil on evaporation of solvent
  3. customwas purified by preparative thin layer chromatography on silica gel (Analtec, 2000 micron, 20×20 plates) by elution with ethyl acetate/hexane in a one to one ratio
  4. customThe isolated product was recrystallized from a 1-chlorobutane and hexane mixture
  5. customto give 0.1 g, m.p. 126°-8°
  6. customThe infrared absorption

Sources & evidence

ORD record
ord-01c2c3a47d1a49d6b1a27f207c00eeb0
Source dataset
uspto-grants-1985_01
Patent number
US04492599

Reaction notes

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