4-Aminophenylsulphur pentafluoride → Dsm-265

HRID 591248Notes

Reaction equation

HRID 591248 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([C:11]([F:14])([F:13])[CH3:12])[N:10]=[C:6]2[N:5]=[C:4]([CH3:15])[CH:3]=1.[NH2:16][C:17]1[CH:22]=[CH:21][C:20]([S:23]([F:28])([F:27])([F:26])([F:25])[F:24])=[CH:19][CH:18]=1>C(O)C>[F:13][C:11]([C:9]1[N:10]=[C:6]2[N:5]=[C:4]([CH3:15])[CH:3]=[C:2]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([S:23]([F:28])([F:24])([F:25])([F:26])[F:27])=[CH:19][CH:18]=3)[N:7]2[N:8]=1)([F:14])[CH3:12]

Participants

4

Reactant 2

HCID 27791904-Aminophenylsulphur pentafluorideHCID 533918697-Chloro-2-(1,1-difluoroethyl)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine

Product 1

HCID 51347395Dsm-265

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of Intermediate 3 (5.84 g, 25.09 mmol) and 4-aminophenylsulfur pentafluoride (MANCHESTER, 5.5 g, 25.09 mmol) in ethanol (150 mL) was heated at 50° C. for 1 h. Heating resulted in the precipitation of a solid. The reaction mixture was concentrated under vacuum, redissolved in DCM (300 mL) and washed with aq. Na2CO3 (2×350 mL). The organic layer was dried over Na2SO4 and filtered. Then 8 g of silica gel were added and the mixture was concentrated under vacuum to dryness. The residue was purified (silica gel column, eluting with Hexane/EtOAc mixtures from 100:0 to 50:50%) to afford the title compound as a white solid.

Workup

  1. temperatureHeating
  2. customresulted in the precipitation of a solid
  3. concentrationThe reaction mixture was concentrated under vacuum
  4. dissolutionredissolved in DCM (300 mL)
  5. washwashed with aq. Na2CO3 (2×350 mL)
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. additionThen 8 g of silica gel were added
  9. concentrationthe mixture was concentrated under vacuum to dryness
  10. customThe residue was purified
  11. wash(silica gel column, eluting with Hexane/EtOAc mixtures from 100:0 to 50:50%)

Sources & evidence

ORD record
ord-75a638764c4b49d1ad54e40031eccb66
Source dataset
uspto-grants-2016_01
Patent number
US09238653B2

Reaction notes

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