Methyl Isocyanate → N-methyl-N'-(4-(1-(2-fluoro-4-biphenylyl)ethyl)thiazol-2-yl)urea

HRID 2072737Notes

Reaction equation

HRID 2072737 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH:7]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:11]([F:21])[CH:10]=2)[CH3:8])[N:6]=1.[CH3:22][N:23]=[C:24]=[O:25]>C(Cl)(Cl)Cl>[CH3:22][NH:23][C:24]([NH:1][C:2]1[S:3][CH:4]=[C:5]([CH:7]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[C:11]([F:21])[CH:10]=2)[CH3:8])[N:6]=1)=[O:25]

Participants

4

Reactant 2

HCID 12228Methyl Isocyanate2×HCID 104699822-Amino-4-(1-(2-fluoro-4-biphenylyl)ethyl)thiazole

Product 1

HCID 15676061N-methyl-N'-(4-(1-(2-fluoro-4-biphenylyl)ethyl)thiazol-2-yl)ureaYield 84%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To 2-amino-4-(1-(2-fluoro-4-biphenylyl)ethyl)thiazole (500 mg, 1.68 mmol) in chloroform (20 ml) was added methylisocyanate (0.10 mg, 1.75 mmol) in chloroform (10 ml) under cooling with ice. After the mixture was stirred, methylisocyanate (0.15 mmol, 2.63 mmol) was added to the mixture, and then the mixture was stirred at room temperature overnight. The mixture was evaporated under reduced pressure to a residue, which was crystallized to afford N-methyl-N'-(4-(1-(2-fluoro-4-biphenylyl)ethyl)thiazol-2-yl)urea (0.499 g, 84% yield) as crystalline material: mp 208.5°-209.0° C.

Workup

  1. temperatureunder cooling with ice
  2. stirringthe mixture was stirred at room temperature overnight
  3. customThe mixture was evaporated under reduced pressure to a residue, which
  4. customwas crystallized

Sources & evidence

ORD record
ord-4273ed96d1e84e5fbbf7bbe288272ddc
Source dataset
uspto-grants-1990_04
Patent number
US04914112

Reaction notes

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