Hydrochloric Acid → (3,4-Dichlorophenyl)(oxazol-5-yl)methanamine hydrochloride
Reaction equation
CC(S(/[N:7]=[CH:8]/[C:9]1[O:13][CH:12]=[N:11][CH:10]=1)=O)(C)C.[Cl:14][C:15]1[CH:16]=[C:17]([Mg]Br)[CH:18]=[CH:19][C:20]=1[Cl:21].[Cl-].[NH4+].Cl.O1CCOCC1>CCOCC.C1(C)C=CC=CC=1>[ClH:14].[Cl:14][C:15]1[CH:16]=[C:17]([CH:8]([C:9]2[O:13][CH:12]=[N:11][CH:10]=2)[NH2:7])[CH:18]=[CH:19][C:20]=1[Cl:21]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -78 °C
Procedure
A dried-flask was charged with 20 (1.211 g, 6.047 mmol) and toluene (5 mL) was added. The reaction was stirred under nitrogen, cooled to −78° C. and (3,4-dichlorophenyl)magnesium bromide (18.14 mL, 9.071 mmol, 0.5M in THF) was added. The reaction was then warmed to −10° C. for 15 min. Saturated ammonium chloride was added and the reaction was extracted with DCM. The organic layer was separated, dried (MgSO4), filtered and concentrated. The resulting residue was dissolved in DCM (10 mL) then 4 N HCl in dioxane (15.12 mL, 60.47 mmol) was added and the solution was stirred for 30 min. The reaction mixture was added dropwise to a stirred solution of ether. The resulting solid was filtered and washed with ether to afford 1.24 g (73.3%) of (3,4-dichlorophenyl)(oxazol-5-yl)methanamine hydrochloride (22).
Workup
- additionwas added
- temperatureThe reaction was then warmed to −10° C. for 15 min
- extractionthe reaction was extracted with DCM
- customThe organic layer was separated
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated
- dissolutionThe resulting residue was dissolved in DCM (10 mL)
- stirringthe solution was stirred for 30 min
- filtrationThe resulting solid was filtered
- washwashed with ether
Sources & evidence
- ORD record
- ord-c504fd30eb1b4b0e8ce455356b245496
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09187462B2
Reaction notes
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