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].[NH4+].[Cl-].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 cooled to −78° C. and (3,4-dichlorophenyl)magnesium bromide (18.14 mL, 9.071 mmol, 0.5 M in THF) was added. The reaction was warmed to −10° C. for 15 min. Saturated NH4Cl was added and the reaction was extracted with DCM. The organic layer was separated, dried, 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 (3,4-dichlorophenyl)(oxazol-5-yl)methanamine hydrochloride (22, 1.24 g, 4.436 mmol, 73.35% yield).
Workup
- additionwas added
- temperatureThe reaction was warmed to −10° C. for 15 min
- extractionthe reaction was extracted with DCM
- customThe organic layer was separated
- customdried
- filtrationfiltered
- concentrationconcentrated
- dissolutionThe resulting residue was dissolved in DCM (10 mL)
- filtrationThe resulting solid was filtered
- washwashed with ether
Sources & evidence
- ORD record
- ord-8681bf735dae4c35bcb683884d9ddc4a
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09133187B2
Reaction notes
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