Benzenesulfonamide → HCID 22923076, compound

HRID 2257699Notes

Reaction equation

HRID 2257699 reaction equation
C1CCN2C(=NCCC2)CC1.[CH3:12][O:13][C:14]([C:16]1[CH:21]=[C:20]([NH:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])[CH:19]=[CH:18][C:17]=1[S:28]([NH2:31])(=[O:30])=[O:29])=[O:15].[CH3:32][O:33][C:34]1[CH:39]=[C:38]([O:40][CH3:41])[N:37]=[C:36]([NH:42][C:43](OC2C=CC=CC=2)=[O:44])[N:35]=1.C1(S(N)(=O)=O)C=CC=CC=1.N1C=CC=NC=1>C(#N)C>[CH3:41][O:40][C:38]1[CH:39]=[C:34]([O:33][CH3:32])[N:35]=[C:36]([NH:42][C:43]([NH:31][S:28]([C:17]2[CH:18]=[CH:19][C:20]([NH:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])=[CH:21][C:16]=2[C:14]([O:13][CH3:12])=[O:15])(=[O:30])=[O:29])=[O:44])[N:37]=1

Participants

7

Reactant 5

HCID 7370BenzenesulfonamideHCID 9260PyrimidineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene2×HCID 10945667Carbamic acid, N-(4,6-dimethoxy-2-pyrimidinyl)-, phenyl esterHCID 22923075HCID 22923075, compound

Product 1

HCID 22923076HCID 22923076, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

0.6 ml of DBU are added dropwise at 0° C. to a mixture of 0.87 g of 2-methoxycarbony1-4-(N-methoxycarbonylmethyl-amino)benzenesulfonamide and 0.90 g of 4,6-dimethoxy-2-phenoxycarbonylaminopyrimidine in 10 ml of acetonitrile. The reaction solution is then stirred at room temperature for 6 h. After removal of the solvent by distillation the residue is taken up in water and washed with diethyl ether. After acidification of the aqueous phase with concentrated hydrochloric acid (pH=1) the sulfonylurea which is separated out is stirred in a little methanol. The colorless solid is separated off by filtration and dried to give 1.18 g of N-[(4,6-dimethoxpyrimidin-2-yl)aminocarbonyl]-2-methoxycarbony1-4-(N-methoxycarbonyl-methylamino)benzenesulfonamide7 m.p.: 184°-186° C. (decomposition). The above process is repeated using the following starting quantities: 31.8 g of the benzene-sulfonamide employed, 58.0 9 of the pyrimidine employed, 150 ml of acetonitrile and 39.4 ml of DBU. After reaction at room temperature for 4 h and work-up as described above, 45.0 g of product with a melting point of 187°-189° C. are obtained.

Workup

  1. customAfter removal of the solvent
  2. distillationby distillation the residue
  3. washwashed with diethyl ether
  4. customAfter acidification of the aqueous phase with concentrated hydrochloric acid (pH=1) the sulfonylurea which is separated out
  5. stirringis stirred in a little methanol
  6. customThe colorless solid is separated off by filtration
  7. customdried
  8. customto give 1.18 g of N-[(4,6-dimethoxpyrimidin-2-yl)aminocarbonyl]-2-methoxycarbony1-4-(N-methoxycarbonyl-methylamino)benzenesulfonamide7 m.p.: 184°-186° C. (decomposition)
  9. customAfter reaction at room temperature for 4 h
  10. customare obtained

Sources & evidence

ORD record
ord-cea483bbe0f244af971d18b9bf77dea0
Source dataset
uspto-grants-1997_08
Patent number
US05658854

Reaction notes

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