Acetic Acid → 8-Bromo-2-(1H-imidazol-2-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene
Reaction equation
[Br:1][C:2]1[CH:17]=[CH:16][C:5]2[C:6]3[N:7]=[C:8]([C:14]#[N:15])[S:9][C:10]=3[CH2:11][CH2:12][O:13][C:4]=2[CH:3]=1.C[O-].[Na+].CO[CH:23](OC)[CH2:24][NH2:25].C(O)(=O)C.Cl>CO.O>[Br:1][C:2]1[CH:17]=[CH:16][C:5]2[C:6]3[N:7]=[C:8]([C:14]4[NH:25][CH:24]=[CH:23][N:15]=4)[S:9][C:10]=3[CH2:11][CH2:12][O:13][C:4]=2[CH:3]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 8-bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carbonitrile (0.100 g, 0.326 mmol) in 1.0 ml of Methanol was added 25% Sodium methoxide (0.020 mL, 0.087 mmol) in Methanol. The reaction was stirred 1 h rt. Aminoacetaldehyde dimethyl acetal (0.0390 mL, 0.358 mmol) was added to the reaction mixture followed by Acetic acid (0.0370 mL, 0.651 mmol). The reaction was heated at 50° C. for 1 h and then cooled to rt. Methanol (0.650 mL, 16.0 mmol) and 6.00 M of Hydrogen chloride in Water (0.163 mL) were added, the reaction was heated 100 for 12 h. The reaction mixture was concentrated then added EtOAc and water. The combined organic layers was concentrated to give 8-Bromo-2-(1H-imidazol-2-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene. MS: (ESI+)=349.1
Workup
- temperatureThe reaction was heated at 50° C. for 1 h
- temperaturecooled to rt
- temperaturethe reaction was heated 100 for 12 h
- concentrationThe reaction mixture was concentrated
- concentrationThe combined organic layers was concentrated
Sources & evidence
- ORD record
- ord-09efcc1e48014e5e97d2e172e3a75eae
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09175009B2
Reaction notes
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