Ammonia → HCID 86647869, compound

HRID 1919601Notes

Reaction equation

HRID 1919601 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]2[NH:6][CH2:7][CH2:8][O:9][C:4]=2[CH:3]=1.[C:12](N1C=CN=C1)([N:14]1C=CN=C1)=[S:13].N>C1COCC1>[Br:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]([C:12](=[S:13])[NH2:14])[CH2:7][CH2:8][O:9][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 802641,1'-ThiocarbonyldiimidazoleHCID 180089607-Bromo-3,4-dihydro-2H-1,4-benzoxazine

Product 1

HCID 86647869HCID 86647869, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 7-bromo-3,4-dihydro-2H-benzo[1,4]oxazine (7.07 g, 33.00 mmol) and 1,1′-thiocarbonyldiimidazole (8.86 g, 49.70 mmol) in THF (83 mL) was heated to 120° C. under microwave irradiation, in a sealed tube, for 20 minutes, and then cooled to r.t. NH3 (110 mL, 7N solution in MeOH, 770 mmol) was added. The reaction mixture was stirred at r.t. for 16 h, and then concentrated in vacuo. The residue was triturated with 1M aqueous HCl, then Et2O, water and again Et2O, and then dried in vacuo to give the title compound (5.31 g, 59%) as a cream solid. δH (DMSO-d6) 8.66-7.53 (2H, m), 7.39 (1H, d, J 8.7 Hz), 7.15 (1H, d, J 2.3 Hz), 7.07 (1H, dd, J 8.9 and 2.3 Hz), 4.30-4.20 (4H, m). LCMS (ES+) 272.9 and 274.9 (M+H)+, RT 3.12 minutes (Method 7).

Workup

  1. temperaturecooled to r.t
  2. concentrationconcentrated in vacuo
  3. customThe residue was triturated with 1M aqueous HCl
  4. dry with materialEt2O, water and again Et2O, and then dried in vacuo

Sources & evidence

ORD record
ord-8150890fcf20491194496cef66c7cb18
Source dataset
uspto-grants-2012_05
Patent number
US08168634B2

Reaction notes

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