Methyl 2-[(4-methoxy-6-methyl-pyrimidin-2-yl)carbamoylsulfamoyl]benzoate → N[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-(n-butylthio)carbonylbenzenesulfonamide

HRID 463989Notes

Reaction equation

HRID 463989 reaction equation
C[Al](C)C.[CH3:5][O:6][C:7]1[CH:12]=[C:11]([CH3:13])[N:10]=[C:9]([NH:14][C:15]([NH:17][S:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27](OC)=[O:28])(=[O:20])=[O:19])=[O:16])[N:8]=1>C1(C)C=CC=CC=1>[CH3:5][O:6][C:7]1[CH:12]=[C:11]([CH3:13])[N:10]=[C:9]([NH:14][C:15]([NH:17][S:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27]([S:18][CH2:21][CH2:22][CH2:23][CH3:24])=[O:28])(=[O:19])=[O:20])=[O:16])[N:8]=1

Participants

4

Reactant 2

HCID 13176578Methyl 2-[(4-methoxy-6-methyl-pyrimidin-2-yl)carbamoylsulfamoyl]benzoateHCID 16682925Trimethylaluminum

Product 1

HCID 13176687N[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-(n-butylthio)carbonylbenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
80 °C

Procedure

Trimethylaluminum (1.5 ml) (2M) was charged via syringe to 5.0 ml dry toluene under nitrogen atmosphere and 0.54 g (0.006 mole) N-butanethiol in 2.0 ml toluene was added dropwise. N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulfonamide (0.95 g) was added portionwise and the mixture warmed to 80° C. for 3 hr. After cooling to room temperature, the mixture was quenched with 25 ml of 10% HCl. Methylene chloride was added, separated, dried over magnesium sulfate, filtered and evaporated to give a crude oil. Trituration with hexanes gave 0.06 white solid, m.p. 115°-120° C., showing infrared absorption peaks at 1725, 1680, 1600, 1560 cm-1 consistent for N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-(N-butylthio)carbonylbenzenesulfonamide.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe mixture was quenched with 25 ml of 10% HCl
  3. additionMethylene chloride was added
  4. customseparated
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customto give a crude oil
  9. customabsorption peaks at 1725, 1680, 1600, 1560 cm-1 consistent for N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-(N-butylthio)carbonylbenzenesulfonamide

Sources & evidence

ORD record
ord-805cc61b588a45f6be58cb1b1d6e3806
Source dataset
uspto-grants-1985_10
Patent number
US04545808

Reaction notes

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