Ammonia → HCID 66665831, compound

HRID 81601Notes

Reaction equation

HRID 81601 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([C:16]([F:19])([F:18])[F:17])[CH2:14][CH2:13][O:12][CH2:11][C:10](=S)[NH:9]1.CO.[NH3:22]>>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([C:16]([F:19])([F:18])[F:17])[CH2:14][CH2:13][O:12][CH2:11][C:10]([NH2:22])=[N:9]1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 86650271HCID 86650271, compound

Product 1

HCID 66665831HCID 66665831, compound

Procedure

5-(2-Fluoro-phenyl)-5-trifluoromethyl-[1,4]oxazepane-3-thione (1.25 g, 4.26 mmol) was dissolved in NH3 solution 7 mol/L in methanol (27 mL, 128 mmol). The sealed reaction vessel was stirred over night at rt. The reaction mixture was evaporated, dissolved in TBME and extracted with 1N HCl. The layers were separated, washed with water and TBME. The aqueous layers were combined, basified by addition of solid K2CO3 and extracted with dichloromethane four times. The combined CH2Cl2 layers were dried over MgSO4.H2O and evaporated to give 1.12 g of the title compound as white crystals.

Workup

  1. customThe sealed reaction vessel
  2. customThe reaction mixture was evaporated
  3. dissolutiondissolved in TBME
  4. extractionextracted with 1N HCl
  5. customThe layers were separated
  6. washwashed with water and TBME
  7. additionbasified by addition of solid K2CO3
  8. extractionextracted with dichloromethane four times
  9. dry with materialThe combined CH2Cl2 layers were dried over MgSO4.H2O
  10. customevaporated

Sources & evidence

ORD record
ord-a407b1b3cd994dbc8007b71e0a90546b
Source dataset
uspto-grants-2014_09
Patent number
US08846658B2

Reaction notes

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