4-(Trifluoromethyl)phenyl isocyanate → HCID 178449549, compound

HRID 2233525Notes

Reaction equation

HRID 2233525 reaction equation
[CH3:1][CH:2]([CH3:15])[CH2:3][NH:4][C:5]1[CH:14]=[CH:13][C:8]2[N:9]=[C:10]([SH:12])[S:11][C:7]=2[CH:6]=1.[F:16][C:17]([F:28])([F:27])[C:18]1[CH:23]=[CH:22][C:21]([N:24]=[C:25]=[O:26])=[CH:20][CH:19]=1>ClCCl>[SH:12][C:10]1[S:11][C:7]2[CH:6]=[C:5]([N:4]([CH2:3][CH:2]([CH3:15])[CH3:1])[C:25]([NH:24][C:21]3[CH:20]=[CH:19][C:18]([C:17]([F:16])([F:27])[F:28])=[CH:23][CH:22]=3)=[O:26])[CH:14]=[CH:13][C:8]=2[N:9]=1

Participants

4

Reactant 2

HCID 737684-(Trifluoromethyl)phenyl isocyanateHCID 178448785HCID 178448785, compound

Product 1

HCID 178449549HCID 178449549, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into 50 ml round bottomed flask were added 6-[(2-methylpropyl)amino]-1,3-benzothiazole-2-thiol (52.36 mg, 0.22 mmol), dichloromethane (10 ml), and α,α,α-trifluoro-p-tolyl isocyanate (41.1 mg, 0.22 mmol). The reaction mixture was stirred 8 h, filtered, and the solid that was obtained was triturated with chloroform, followed with chloroform/methanol (9:1 mixture) to give 60 mg (64%) of the title compound. 1H NMR (DMSO-d6) δ=0.84 (d, 6H), 1.66 (m, 1H), 3.49 (d, 2H), 7.30 (s, 2H), 7.50 (d, 2H), 7.60 (d, 2H), 7.71 (s, 1H); ESIMS: m/z 424 (M−H).

Workup

  1. filtrationfiltered
  2. customthe solid that was obtained
  3. customwas triturated with chloroform

Sources & evidence

ORD record
ord-032960613f994cabbfb4e47b69492968
Source dataset
uspto-grants-2010_05
Patent number
US07709510B2

Reaction notes

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