Acetonitrile → HCID 11079555, compound

HRID 650038Notes

Reaction equation

HRID 650038 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:22][CH3:23])=[C:6]([NH:8][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)=[N:10][NH2:11])[CH:7]=1.[C:24](N1C=CN=C1)(N1C=CN=C1)=[S:25].[K+].[Br-].CC#N>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:22][CH3:23])=[C:6]([N:8]2[C:9]([C:12]3[CH:13]=[CH:14][C:15]([C:18]([F:20])([F:21])[F:19])=[CH:16][CH:17]=3)=[N:10][NH:11][C:24]2=[S:25])[CH:7]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 802641,1'-ThiocarbonyldiimidazoleHCID 253877Potassium BromideHCID 178490717HCID 178490717, compound

Product 1

HCID 11079555HCID 11079555, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(5-Chloro-2-methoxyphenyl)-4-(trifluoromethyl)benzene carbohydrazonamide (2.5 g, 7.27 mmol) was dissolved in THF (450 ml) under N2 and 1,1′-thiocarbonyldiimidazole (1.95 g, 11.0 mmol) added. The solution was stirred at reflux for 18 h and solvent removed by rotary evaporation. The residue was taken up in ethyl acetate (400 ml) and washed with 0.1N HCl solution (100 ml), water (100 ml) and brine prior to drying over MgSO4. Recrystallization from acetonitrile gave 1.91 g (68%) mp 275-280° C.; IR(KBr, υ=cm−1) 3080, 3058, 3020, 2916, 1506, 1488, 1322, 1288, 1174, 1130, 1110; 1H NMR (300 MHz, DMSO-d6) δ 3.51 (3H, s), 7.17 (1H, d, J=9.0 Hz), 7.53-7.57 (3H, m), 7.69 (1H, d, J=2.6 Hz), 7.77 (2H, d, J=8.4 Hz.s), 14.29 (1H, s); MS(DCl)m/z: 386(MH+). Anal. calcd. for C16H11ClF3N3OS.0.06 CH3CN: C, 49.87; H, 2.90; N, 11.04. Found: C, 50.03; H, 2.94; N, 11.07.

Workup

  1. temperatureat reflux for 18 h
  2. customsolvent removed by rotary evaporation
  3. washwashed with 0.1N HCl solution (100 ml), water (100 ml) and brine
  4. dry with materialto drying over MgSO4
  5. customRecrystallization from acetonitrile
  6. customgave 1.91 g (68%) mp 275-280° C.

Sources & evidence

ORD record
ord-2fb27b401d0d407eafd9185ae81953ac
Source dataset
uspto-grants-2001_08
Patent number
US06271249B1

Reaction notes

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