Phosgene → 5-(3-Fluoro-4-methanesulfonyl-phenyl)-2-isocyanato-4-methyl-thiazole

HRID 1092979Notes

Reaction equation

HRID 1092979 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:12]2[S:16][C:15]([NH2:17])=[N:14][C:13]=2[CH3:18])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].[C:19](Cl)(Cl)=[O:20]>C(#N)C>[F:1][C:2]1[CH:3]=[C:4]([C:12]2[S:16][C:15]([N:17]=[C:19]=[O:20])=[N:14][C:13]=2[CH3:18])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:9])=[O:10]

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 573512775-(3-Fluoro-4-(methylsulfonyl)phenyl)-4-methylthiazol-2-amine

Product 1

HCID 858616485-(3-Fluoro-4-methanesulfonyl-phenyl)-2-isocyanato-4-methyl-thiazole

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

5-(3-Fluoro-4-methanesulfonyl-phenyl)-4-methyl-thiazol-2-ylamine (Example 72) (1.74 mmol, 0.5 g) is added to acetonitrile (15 ml) and treated with phosgene (20% solution in toluene, 6.99 mmol, 3.7 ml). The reaction mixture is heated to reflux (85° C.) for 30 minutes. After cooling to room temperature the solvent is removed in vacuo to leave 5-(3-fluoro-4-methanesulfonyl-phenyl)-2-isocyanato-4-methyl-thiazole as an orange solid.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureAfter cooling to room temperature the solvent
  3. customis removed in vacuo

Sources & evidence

ORD record
ord-5ff5a80d4c784c1a9899e40ed1deb7f1
Source dataset
uspto-grants-2012_03
Patent number
US08129541B2

Reaction notes

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