Phosgene → HCID 19101091, compound

HRID 1975231Notes

Reaction equation

HRID 1975231 reaction equation
[CH2:1]([NH:5][C:6](=[O:23])[NH:7][S:8]([C:11]1[C:16]([N:17]([CH3:22])[S:18]([CH3:21])(=[O:20])=[O:19])=[CH:15][CH:14]=[CH:13][N:12]=1)(=[O:10])=[O:9])CCC.C(Cl)(Cl)=O.[CH3:28][O:29][C:30]1[CH:35]=[C:34]([O:36][CH3:37])[N:33]=[C:32](NC)[N:31]=1>ClC1C=CC=CC=1.ClCCl>[CH3:28][O:29][C:30]1[CH:35]=[C:34]([O:36][CH3:37])[N:33]=[C:32]([N:5]([CH3:1])[C:6](=[O:23])[NH:7][S:8]([C:11]2[C:16]([N:17]([CH3:22])[S:18]([CH3:21])(=[O:19])=[O:20])=[CH:15][CH:14]=[CH:13][N:12]=2)(=[O:9])=[O:10])[N:31]=1

Participants

6

Reactant 3

HCID 6371Phosgene2×HCID 676475HCID 676475, compoundHCID 11111279HCID 11111279, compound

Product 1

HCID 19101091HCID 19101091, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7964ChlorobenzeneSolvent

Conditions

Temperature
70 °C

Procedure

63.0 g (0.17 mol) of 3-butyl-1-[3-(N-methyl-N-methylsulfonylamino)-2-pyridylsulfonyl]urea are suspended in 1 l of chlorobenzene, and the suspension is heated to 70° C. At this temperature, the experiment starts to pass a gentle stream of phosgene into the suspension, and heating is continued for approx. 20 minutes until an internal temperature of 120° C. is reached. After phosgene has been passed in for a further 20 minutes (approx. 50 g (0.5 mol) in total), the lower-boiling components together with approx. 300 ml of chlorobenzene are removed from the reaction mixture by distillation over a period of 30 minutes. After the mixture has cooled to room temperature, 29.0 g (0.17 mol) of 4,6-dimethoxy-2-methylaminopyrimidine dissolved in 500 ml of dichloromethane are added, and the mixture is heated for 7 hours at 40° C. The mixture is cooled, the organic phase is washed with 1×250 ml each of 1N HCl and water, dried and evaporated. After the crude product has been triturated with diethyl ether, 66.6 g (85% of theory) of 3-(4,6-dimethoxypyrimidin-2-yl)-3-methyl-1-[3-(N-methyl-N-methylsulfonyl-amino)-2-pyridyloulfonyl]-urea of m.p. 167°-168° C. (decomp.) remained.

Workup

  1. temperatureheating
  2. customhas been passed in for a further 20 minutes (approx. 50 g (0.5 mol) in total)
  3. customthe lower-boiling components together with approx. 300 ml of chlorobenzene are removed from the reaction mixture by distillation over a period of 30 minutes
  4. temperatureAfter the mixture has cooled to room temperature
  5. additionare added
  6. temperaturethe mixture is heated for 7 hours at 40° C
  7. temperatureThe mixture is cooled
  8. washthe organic phase is washed with 1×250 ml each of 1N HCl and water
  9. customdried
  10. customevaporated
  11. customAfter the crude product has been triturated with diethyl ether, 66.6 g (85% of theory) of 3-(4,6-dimethoxypyrimidin-2-yl)-3-methyl-1-[3-(N-methyl-N-methylsulfonyl-amino)-2-pyridyloulfonyl]-urea of m.p. 167°-168° C. (decomp.)

Sources & evidence

ORD record
ord-07482e6ccff64e06ba6284b6d05088f0
Source dataset
uspto-grants-1994_02
Patent number
US05284945

Reaction notes

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