Hydrochloric Acid → HCID 178515999, compound
Reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10](=O)[CH:11]=[CH:12][CH:13]1[CH2:22][CH2:21][C:16]2(OCC[O:17]2)[CH2:15][CH2:14]1.Cl.C(=O)(O)[O-].[Na+]>O1CCOCC1>[Br:8][C:6]1[CH:5]=[CH:4][C:3]2[NH:9][C:10]([CH:11]=[CH:12][CH:13]3[CH2:22][CH2:21][C:16](=[O:17])[CH2:15][CH2:14]3)=[N:1][C:2]=2[CH:7]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
A solution of N-(2-amino-4-bromo-phenyl)-3-(1,4-dioxa-spiro[4.5]dec-8-yl)-acrylamide (6.0 g, 28 mmol, prepared as in STEP D above) in 1,4-dioxane (100 mL) was treated with 1N HCl (30 mL, 30 mmol). The resulting solution was stirred at 100° C. for 1 h and then allowed to cool to room temperature. The resulting mixture was made basic with saturated aqueous sodium bicarbonate and extracted thrice with ethyl acetate. The ethyl acetate layers were combined and washed successively with water and brine, separated, dried over sodium sulfate, filtered and concentrated. The residue was taken up in ethyl acetate and applied to a silica gel plug (100 g) equilibrated with ethyl acetate and eluted with ethyl acetate. The desired fractions were pooled, concentrated and dried in vacuo to yield 4-[2-(5-bromo-1H-benzimidazol-2-yl)-vinyl]-cyclohexanone.
Workup
- temperatureto cool to room temperature
- extractionextracted thrice with ethyl acetate
- washwashed successively with water and brine
- customseparated
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- washeluted with ethyl acetate
- concentrationconcentrated
- customdried in vacuo
Sources & evidence
- ORD record
- ord-9305519d63774b4c9472f41b8caa6c96
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08217060B2
Reaction notes
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