2-Fluoro-5-methylphenyl isocyanate → HCID 86689235, compound

HRID 871029Notes

Reaction equation

HRID 871029 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]#[N:14])=[C:11]([Cl:15])[S:10][N:9]=2)=[CH:4][CH:3]=1.[F:16][C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][C:18]=1[N:24]=[C:25]=[O:26]>C1COCC1>[Cl:15][C:11]1[S:10][N:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:1][C:25]([NH:24][C:18]3[CH:19]=[C:20]([CH3:23])[CH:21]=[CH:22][C:17]=3[F:16])=[O:26])=[CH:3][CH:4]=2)[C:12]=1[C:13]#[N:14]

Participants

4

Reactant 2

HCID 27333772-Fluoro-5-methylphenyl isocyanate2×HCID 86689236HCID 86689236, compound

Product 1

HCID 86689235HCID 86689235, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-(4-amino-phenyl)-5-chloro-isothiazole-4-carbonitrile (4.565 g, 19.4 mmol) and 2-fluoro-5-methylphenyl isocyanate (5.85 g, 38.7 mmol) in 100 mL of dry THF was heated to reflux overnight. TLC indicated presence of considerable amount of starting material. Additional 2 g of 2-fluoro-5-methylphenyl isocyanate was added and the reaction was continued for another 24 h. The reaction was cooled to room temperature. THF was removed in vacuo and the resulting solid was stirred in 200 mL of Et2O for 1 h. Product was collected by filtration and washed with Et2O/hexanes to afford the title compound as a light yellow solid (6.78 g, 90%).

Workup

  1. temperatureto reflux overnight
  2. customTHF was removed in vacuo
  3. filtrationProduct was collected by filtration
  4. washwashed with Et2O/hexanes

Sources & evidence

ORD record
ord-77c64fcdd6074d43a9d382fb4e5d9b44
Source dataset
uspto-grants-2015_03
Patent number
US08969583B2

Reaction notes

Loading…