HCID 10900913, compound → HCID 15335013, compound

HRID 368928Notes

Reaction equation

HRID 368928 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([N:12]=[C:13]=[O:14])(=[O:11])=[O:10].[Cl:17][C:18]1[CH:23]=[C:22]([C:24]2[N:25]=[C:26]([NH2:29])[S:27][CH:28]=2)[CH:21]=[C:20]([Cl:30])[N:19]=1>C(#N)C>[Cl:17][C:18]1[CH:23]=[C:22]([C:24]2[N:25]=[C:26]([NH:29][C:13]([NH:12][S:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[C:2]([F:15])([F:1])[F:16])(=[O:11])=[O:10])=[O:14])[S:27][CH:28]=2)[CH:21]=[C:20]([Cl:30])[N:19]=1

Participants

4

Reactant 2

HCID 10900913HCID 10900913, compoundHCID 11817579Benzenesulfonyl isocyanate, 2-(trifluoromethyl)-

Product 1

HCID 15335013HCID 15335013, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

7.53 g (0.03 mol) of 2-trifluoromethylphenylsulphonyl isocyanate are added to a solution of 7.38 g (0.03 mol) of [4-(2,6-dichloropyridin-4-yl)-thiazol-2-yl]-amine in 180 ml of acetonitrile at 75° C. in the course of 5 minutes, while stirring. The reaction mixture is stirred at 75° C. for a further 3 hours and then cooled to room temperature, and the solid which has precipitated out is filtered off with suction, washed twice with 10 ml of acetonitrile each time and dried at 45° C. under reduced pressure. 14 g (93.9% of theory) of N-[4-(2,6-dichloro-pyridin-4-yl)-thiazol-2-yl]-N'-(2-trifluoromethyl-phenylsulphonyl)-urea are obtained in this manner in the form of a solid substance with a melting point of >280° C.

Workup

  1. stirringThe reaction mixture is stirred at 75° C. for a further 3 hours
  2. customthe solid which has precipitated out
  3. filtrationis filtered off with suction
  4. washwashed twice with 10 ml of acetonitrile each time
  5. customdried at 45° C. under reduced pressure

Sources & evidence

ORD record
ord-d4b104601dc14dac96c8d2a8f5ded332
Source dataset
uspto-grants-2000_10
Patent number
US06136754

Reaction notes

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