Thiourea → 2-Amino-4-(3-phthalimidopropyl)thiazole
Reaction equation
Br[CH2:2][C:3](=O)[CH2:4][CH2:5][CH2:6][N:7]1[C:11](=[O:12])[C:10]2=[CH:13][CH:14]=[CH:15][CH:16]=[C:9]2[C:8]1=[O:17].[NH2:19][C:20]([NH2:22])=[S:21]>CN(C=O)C>[NH2:22][C:20]1[S:21][CH:2]=[C:3]([CH2:4][CH2:5][CH2:6][N:7]2[C:11](=[O:12])[C:10]3=[CH:13][CH:14]=[CH:15][CH:16]=[C:9]3[C:8]2=[O:17])[N:19]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
1-bromo-5-phthalimido-2-pentanone (0.500 g, 1.61 mmol) was dissolved in DMF (3.5 mL) at 0° C. and thiourea (0.135 g, 1.77 mmol) was added drop-wise as a solution in DMF (0.50 mL). The solution was allowed to warm to room temperature and stirring was continued for 2 h at which time the DMF was removed under reduced pressure and the resulting slurry was made alkaline with 10% K2CO3 (100 mL). The aqueous solution was then extracted with EtOAc (3×40 mL) and the organic layer was washed with brine (50 mL), dried (Na2SO4), filtered and concentrated to obtain 51 (448 mg, 97%) as a fine white powder in its freebase form: 1H NMR (300 MHz, DMSO-d6) δ 7.85 (m, 4H), 6.78 (s, 2H), 6.13 (s, 1H), 3.56 (t, 2H, J=6.9 Hz), 2.42 (t, 2H, J=7.5 Hz), 1.88 (quint., 2H, J=7.5 Hz); 13C NMR (75 MHz, DMSO-d6) δ 168.01, 167.87, 151.20, 134.25, 131.61, 122.89, 100.17, 37.27, 28.70, 27.09; HRMS (ESI) calcd for C14H14N3O2S (MH+) 288.0801, found 288.0799.
Workup
- customthe DMF was removed under reduced pressure
- extractionThe aqueous solution was then extracted with EtOAc (3×40 mL)
- washthe organic layer was washed with brine (50 mL)
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-14bda1d1ea59465db8f2510abe686dd1
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08927029B2
Reaction notes
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