Ammonia → 5-(3-Bromo-phenyl)-5-difluoromethyl-5,6-dihydro-2H-[1,4]oxazin-3-ylamine

HRID 221691Notes

Reaction equation

HRID 221691 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([CH:15]([F:17])[F:16])[NH:13][C:12](=S)[CH2:11][O:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[NH3:18]>CO>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([CH:15]([F:17])[F:16])[CH2:9][O:10][CH2:11][C:12]([NH2:18])=[N:13]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 86650255HCID 86650255, compound

Product 1

HCID 668881845-(3-Bromo-phenyl)-5-difluoromethyl-5,6-dihydro-2H-[1,4]oxazin-3-ylamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-(3-Bromo-phenyl)-5-difluoromethyl-morpholine-3-thione (7.49 g, 23.25 mmol) was dissolved in 36 ml 7N NH3 in methanol and stirred at room temperature for 18 h. After completion, volatiles were removed under reduced pressure to yield the title compound. 1H-NMR (360 MHz, DMSO-d6): 7.80 (s, 1H), 7.52 (m, 2H), 7.33 (m, 1H), 6.25 (br, 2H, NH2), 6.04 (t, 1H, CHF2), 4.15-3.90 (m, 2H), 3.72 (d, 1H), 3.45 (d, 1H); MS: 305 [(M+)+].

Workup

  1. customAfter completion, volatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-d0a697b6edca4c888af894510a4883db
Source dataset
uspto-grants-2012_06
Patent number
US08207164B2

Reaction notes

Loading…