Triethylamine → 1-{[o-(Cyclopropylcarbonyl)phenyl]sulfamoyl}-3-(4,6-dichloro-2-pyrimidinyl)urea

HRID 744889Notes

Reaction equation

HRID 744889 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[N:3]=1.Cl[S:11]([N:14]=[C:15]=[O:16])(=[O:13])=[O:12].[CH:17]1([C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[NH2:28])=[O:21])[CH2:19][CH2:18]1.C(N(CC)CC)C>C(Cl)Cl>[CH:17]1([C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[NH:28][S:11]([NH:14][C:15]([NH:1][C:2]2[N:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[N:3]=2)=[O:16])(=[O:13])=[O:12])=[O:21])[CH2:18][CH2:19]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 655222-Amino-4,6-dichloropyrimidineHCID 70918Chlorosulfonyl isocyanateHCID 10931741(2-Aminophenyl)(cyclopropyl)methanone

Product 1

HCID 110263731-{[o-(Cyclopropylcarbonyl)phenyl]sulfamoyl}-3-(4,6-dichloro-2-pyrimidinyl)ureaYield 88.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-Amino-4,6-dichloropyrimidine (6.15 g, 0.0375 mol) is added portionwise to a solution of chlorosulfonyl isocyanate (5.30 g, 0.0375 mol) in methylene chloride at 0° C. The resulting mixture is stirred at 0° to 2° C. for two hours and a solution of o-aminophenyl cyclopropyl ketone (6.04 g, 0.0375 mol) and triethylamine (3.8 g, 0.0406 mol) in methylene chloride is slowly added to the mixture. The resulting solution is stirred at room temperature overnight, washed with water, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain the title product as a yellow solid (14.3 g, 75% real by HPLC analysis, 68% yield) which is used as a starting material for Example 2 without purification. A portion of the yellow solid is purified to yield the title product, mp 114°-116° C.

Workup

  1. stirringThe resulting solution is stirred at room temperature overnight
  2. washwashed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-314f6b230d654128a1112661519cb201
Source dataset
uspto-grants-1996_09
Patent number
US05559234

Reaction notes

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