Sodium Hydroxide → ((2,3-Dimethylphenyl)methyl)-1,3-thiazolin-2-ylamine
Reaction equation
[OH-].[Na+].Cl.[CH3:4][C:5]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:12][NH:13][C:14]1[S:15][CH2:16][CH2:17][N:18]=1>O.C(OCC)C>[CH3:4][C:5]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:12][NH:13][C:14]1[S:15][CH2:16][CH2:17][N:18]=1Participants
Procedure
A mixture of 1.4 grams (0.034 mole) of sodium hydroxide in 100 mL of water was added to a stirred, cold (ice water bath) mixture of 8.0 grams (0.031 mole) of ((2,3-dimethylphenyl)methyl)-1,3-thiazolin-2-ylamine hydrochloride (Compound C11) in 100 mL of diethyl ether. The reaction mixture was allowed to warm to ambient temperature where it stirred for two hours. The reaction mixture was poured into a separatory funnel and the organic phase was removed and saved. The aqueous phase was extracted with 100 mL of diethyl ether. The organic extract was combined with the saved organic phase, dried with sodium sulfite and filtered. The filtrate was concentrated under reduced pressure to yield 6.8 grams of the title compound as a white solid, melting point 110-114° C. The NMR spectrum was consistent with the proposed structure.
Workup
- additionThe reaction mixture was poured into a separatory funnel
- customthe organic phase was removed
- extractionThe aqueous phase was extracted with 100 mL of diethyl ether
- extractionThe organic extract
- dry with materialdried with sodium sulfite
- filtrationfiltered
- concentrationThe filtrate was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-0a74d17aec6e4360a8b38730d97d3d46
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08193118B2
Reaction notes
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