Potassium Carbonate → Methyl 2-[[(4,6-dichloropyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzeneacetate

HRID 1262971Notes

Reaction equation

HRID 1262971 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11]([NH2:14])(=[O:13])=[O:12].C(=O)([O-])[O-].[K+].[K+].[Cl:22][C:23]1[CH:28]=[C:27]([Cl:29])[N:26]=[C:25]([N:30]=[C:31]=[O:32])[N:24]=1>C(#N)C.O>[Cl:29][C:27]1[CH:28]=[C:23]([Cl:22])[N:24]=[C:25]([NH:30][C:31]([NH:14][S:11]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH2:4][C:3]([O:2][CH3:1])=[O:15])(=[O:12])=[O:13])=[O:32])[N:26]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 123646504,6-Dichloro-2-isocyanatopyrimidineHCID 13064551Methyl 2-(2-sulfamoylphenyl)acetate

Product 1

HCID 13064559Methyl 2-[[(4,6-dichloropyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzeneacetateYield 45.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To 2.3 g of 2-(aminosulfonyl)benzeneacetic acid methyl ester in 30 ml of acetonitrile was added 1.5 g of anhydrous potassium carbonate and 1.6 g of 4,6-dichloropyrimidin-2-yl isocyanate. The mixture was stirred at room temperature for 6 hours, diluted with 250 g of water and acidified to a pH of about 4. The resulting solid was filtered and dried to yield 1.6 g of methyl 2-[[(4,6-dichloropyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzeneacetate, a pale yellow solid, m.p. 115°-118° C. It showed infrared absorption peaks at 1730, 1600 and 1560 cm-1 and nuclear magnetic resonance peaks at 3.7 ppm, methyl ester group; 4.2 ppm, benzeneacetic group; 6.9 ppm, pyrimidin H; 7.4-7.6 ppm, aromatic hydrogens; consistent for the product.

Workup

  1. filtrationThe resulting solid was filtered
  2. customdried

Sources & evidence

ORD record
ord-696ee197f2764156859fd7d87ef86e66
Source dataset
uspto-grants-1984_06
Patent number
US04454335

Reaction notes

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