Thiourea → HCID 18790607, compound

HRID 1107003Notes

Reaction equation

HRID 1107003 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][NH:13][C:14](=[O:19])[C:15]([F:18])([F:17])[F:16])=[CH:7][CH:6]=1)=O.[NH2:20][C:21]([NH2:23])=[S:22]>C(O)(C)C>[NH2:23][C:21]1[S:22][CH:2]=[C:3]([C:5]2[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][NH:13][C:14](=[O:19])[C:15]([F:18])([F:17])[F:16])=[CH:7][CH:6]=2)[N:20]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 18790603HCID 18790603, compound

Product 1

HCID 18790607HCID 18790607, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

The title compound: A solution of N-{2-{4-(2-bromoacetyl)phenyl}ethyl}-2,2,2,-trifluoroacetamide (1.00 g, 2.96 mmol), prepared in the preceding section (c), and thiourea (225 mg, 2.96 mmol) in isopropanol (30 mL) was heated at reflux for 1 h. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in a mixture of EtOAc and aqueous 10% HCl and the phases were separated. The aqueous layer was washed with EtOAc then rendered basic with solid K2CO3. The resulting mixture was extracted with EtOAc. The organic layer was dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash chromatography (SiO2, EtOAc:Hexane, 1:1) to give N-{2-{4-(2-amino-4-thiazolyl)phenyl}ethyl}-2,2,2-trifluoroacetamide (240 mg, 26% yield): M.p. 180-182°; 1H NMR (DMSO-d6) δ 9.48 (broad t, J=5.4 Hz, 1H), 7.72 (d, J=8.4 Hz, 2H), 7.19 (d, J=8.4 Hz, 2H), 7.00 (broad s, 2H), 6.95 (s, 1H), 3.43 (broad q, J=6.8 Hz, 2H), 2.80 (t, J=7.2 Hz, 2H); MS (FAB) m/z 316 (MH)+ ; Anal. Calcd for C13H12F3N3OS: C, 49.52; H, 3.84; N, 13.33; S, 10.17. Found: C, 49.69; H, 3.82; N, 13.36; S, 10.00.

Sources & evidence

ORD record
ord-ed8b6330266f4858bc7f67eb95ae5fbb
Source dataset
uspto-grants-2000_05
Patent number
US06057451

Reaction notes

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