Hydrochloric Acid → 5-[2-[(Cyclohexyloxy)methyl]phenyl]-2-thiazolamine
Reaction equation
Cl.[CH:2]1([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]2[S:20][C:19]([N:21]=C(C3C=CC=CC=3)C3C=CC=CC=3)=[N:18][CH:17]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1>CO>[CH:2]1([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]2[S:20][C:19]([NH2:21])=[N:18][CH:17]=2)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
75 ml of an aqueous hydrochloric acid solution (1 M) are added to 11 g of 5-{-2-[(cyclohexyloxy)methyl]phenyl}-N-(diphenylmethylene)-1,3-thiazol-2-amine, obtained in step 1.4, in solution in 150 ml of methanol, and the mixture is stirred for 18 hours at 20° C. The mixture is evaporated to dryness, the residue is taken up in diethyl ether and washed with an aqueous sodium hydroxide solution (0.5 M). The organic phase is dried over anhydrous sodium sulfate and concentrated. The residue is chromatographed on a silica gel column, eluting with a dichloromethane/methanol 98/2 (v/v) mixture, to give 5.3 g of a beige-colored solid. m.p.=102° C.
Workup
- customThe mixture is evaporated to dryness
- washwashed with an aqueous sodium hydroxide solution (0.5 M)
- dry with materialThe organic phase is dried over anhydrous sodium sulfate
- concentrationconcentrated
- customThe residue is chromatographed on a silica gel column
- washeluting with a dichloromethane/methanol 98/2 (v/v) mixture
Sources & evidence
- ORD record
- ord-3f148f26b039450c9c26652699bda7ad
- Source dataset
- uspto-grants-2007_10
- Patent number
- US07288659B2
Reaction notes
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