HCID 10900913, compound → HCID 15335013, compound

HRID 1586389Notes

Reaction equation

HRID 1586389 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-pyridin4-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-d5e2084156c84ca39cb565d88024be46
Source dataset
uspto-grants-1999_08
Patent number
US05945380

Reaction notes

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