Water → HCID 178434968, compound

HRID 1404866Notes

Reaction equation

HRID 1404866 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[C:3]=1[NH:12][C:13]([NH:15]/[N:16]=[CH:17]/[C:18]1[CH:23]=[CH:22][C:21]([C:24]2[N:28]=[CH:27][N:26]([C:29]3[CH:34]=[CH:33][C:32]([O:35][C:36]([F:39])([F:38])[F:37])=[CH:31][CH:30]=3)[N:25]=2)=[CH:20][CH:19]=1)=[S:14].Cl[CH2:41][C:42](=[O:44])[CH3:43].C(N(CC)CC)C.O>CC(=O)CC>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[C:3]=1/[N:12]=[C:13]1\[S:14][CH2:41][C:42]([CH3:43])([OH:44])[N:15]\1/[N:16]=[CH:17]/[C:18]1[CH:23]=[CH:22][C:21]([C:24]2[N:28]=[CH:27][N:26]([C:29]3[CH:34]=[CH:33][C:32]([O:35][C:36]([F:38])([F:39])[F:37])=[CH:31][CH:30]=3)[N:25]=2)=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6571ChloroacetoneHCID 8471TriethylamineHCID 89723814HCID 89723814, compound

Product 1

HCID 178434968HCID 178434968, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of (E)-N-(2-chloro-6-(trifluoromethyl)phenyl)-2-(4-(1-(4-(trifluoromethoxy)-phenyl)-1H-1,2,4-triazol-3-yl)benzylidene)hydrazinecarbothioamide (111 mg, 0.19 mmol) in butanone (2 mL) was added chloroacetone (0.02 mL, 0.27 mmol) and triethylamine (0.05 mL, 0.38 mmol), and the reaction was stirred at 75° C. for 16 hours. The mixture was allowed to cool to room temperature, transferred to a separatory funnel containing water (5 mL), and was extracted twice with dichloromethane. The organic extracts were filtered through a phase separator, adsorbed onto silica gel, and purified by flash chromatography (0-20% ethyl acetate/B, where B=1:1 dichloromethane/hexanes). The title compound was isolated as a yellow solid (60.5 mg, 50%): mp 97° C. (dec); 1H NMR (400 MHz, CDCl3) δ 9.72-9.57 (m, 1H), 8.58 (s, 1H), 8.24 (d, J=8.4 Hz, 2H), 7.88-7.72 (m, 4H), 7.56 (dt, J=18.3, 5.8 Hz, 2H), 7.40 (d, J=8.3 Hz, 2H), 7.09 (t, J=8.0 Hz, 1H), 3.49 (d, J=13.3 Hz, 1H), 3.35 (m, 2H), 1.86 (d, J=14.0 Hz, 3H); 19F NMR (376 MHz, CDCl3) δ−58.01, −62.05, −62.22; ESIMS m/z 642 (M+H).

Workup

  1. temperatureto cool to room temperature
  2. customtransferred to a separatory funnel
  3. extractionwas extracted twice with dichloromethane
  4. filtrationThe organic extracts were filtered through a phase separator
  5. custompurified by flash chromatography (0-20% ethyl acetate/B, where B=1:1 dichloromethane/hexanes)

Sources & evidence

ORD record
ord-680223c5d2b54ebfb2c23dece31f9b56
Source dataset
uspto-grants-2014_12
Patent number
US08916183B2

Reaction notes

Loading…