Diiodomethane → HCID 140650525, compound

HRID 1475608Notes

Reaction equation

HRID 1475608 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[NH:9][C:10]([NH:12]/[N:13]=[CH:14]/[C:15]1[CH:20]=[CH:19][C:18]([C:21]2[N:25]=[CH:24][N:23]([C:26]3[CH:31]=[CH:30][C:29]([O:32][C:33]([F:36])([F:35])[F:34])=[CH:28][CH:27]=3)[N:22]=2)=[CH:17][CH:16]=1)=[S:11].[C:37](=O)([O-])[O-].[K+].[K+].ICI>CC(=O)CC.C(Cl)Cl>[F:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3]=1[N:9]1[CH2:37][S:11]/[C:10]/1=[N:12]/[N:13]=[CH:14]\[C:15]1[CH:20]=[CH:19][C:18]([C:21]2[N:25]=[CH:24][N:23]([C:26]3[CH:31]=[CH:30][C:29]([O:32][C:33]([F:35])([F:34])[F:36])=[CH:28][CH:27]=3)[N:22]=2)=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 6346DiiodomethaneHCID 11430Potassium CarbonateHCID 88590284HCID 88590284, compound

Product 1

HCID 140650525HCID 140650525, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
55 °C

Procedure

To a mixture of (E)-N-(2,6-difluorophenyl)-2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)benzylidene)hydrazinecarbothioamide (0.50 g, 0.96 mmol) and potassium carbonate (0.53 g, 3.9 mmol) in butanone (10 mL) in a 25 mL vial equipped with a magnetic stir bar was added diiodomethane (0.093 ml, 1.2 mmol). The reaction was heated to 55° C. and stirred for two days. The reaction mixture was diluted with DCM, washed with water, and the phases separated. The aqueous phase was extracted with DCM and the combined organic phases were dried by passing through a phase separator cartridge and then concentrated. Purification by flash column chromatography provided a yellow oil which crystallized upon standing. The solid was slurried in diethyl ether and hexanes and collected by vacuum filtration. The solid was washed with hexanes and dried to provide the title compound (0.086 g, 0.16 mmol, 17%) as a light yellow solid: mp 144-146° C.; 1H NMR (400 MHz, CDCl3) δ 8.58 (s, 1H), 8.34 (s, 1H), 8.20 (d, J=8.3 Hz, 2H), 7.81 (d, J=8.8 Hz, 4H), 7.40 (d, J=8.3 Hz, 2H), 7.31-7.23 (m, 1H), 7.03-6.97 (m, 2H), 5.05 (s, 2H); ESIMS m/z 532 (M+H).

Workup

  1. customvial equipped with a magnetic stir bar
  2. washwashed with water
  3. customthe phases separated
  4. extractionThe aqueous phase was extracted with DCM
  5. customthe combined organic phases were dried
  6. concentrationconcentrated
  7. customPurification by flash column chromatography
  8. customprovided a yellow oil which
  9. customcrystallized
  10. filtrationhexanes and collected by vacuum filtration
  11. washThe solid was washed with hexanes
  12. customdried

Sources & evidence

ORD record
ord-ef49622a8130457297fabb34c0a7af69
Source dataset
uspto-grants-2015_04
Patent number
US09018388B2

Reaction notes

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