1-Bromo-2-butanone → 2-[4-(Benzyloxy)-3-propylphenyl]-4-ethyl-1,3-thiazole

HRID 603385Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[S:17])[NH2:16])=[CH:11][C:10]=1[CH2:18][CH2:19][CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:22][C:23](=O)[CH2:24][CH3:25]>CCO>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[S:17][CH:22]=[C:23]([CH2:24][CH3:25])[N:16]=2)=[CH:11][C:10]=1[CH2:18][CH2:19][CH3:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 4-(benzyloxy)-3-propylbenzenecarbothioamide (0.53 g, 1.86 mmol) (Example 31) in EtOH (70 mL) was added 1-bromo-2-butanone (0.47 g, 2.79 mmol), and the reaction was stirred for 3 h at 70° C. After the reaction was complete, the reaction mixture was concentrated under reduced pressure and the residue was saved. This procedure was repeated on a 1.1 g scale (based on thioamide). The two crude residues were combined and purified by silica gel chromatography (EtOAc/hexane (v/v)=1:9, then 100% EtOAc) to give 0.87 g (67% overall) of the title compound. 1H NMR (400 MHz, CDCl3):δ 7.72 (s, 1H), 7.67 (d, 1H), 7.45-7.28 (m, 5H), 6.88 (d, 1H), 6.76 (s, 1H), 5.12 (s, 2H), 4.09 (q, 2H), 2.84 (q, 2H), 2.75-2.66 (m, 2H), 1.30 (t, 3H), 0.93 (t, 3H).

Workup

concentrationthe reaction mixture was concentrated under reduced pressure
custompurified by silica gel chromatography (EtOAc/hexane (v/v)=1:9

Sources & evidence

ORD record: ord-7c70bb110b1147b8836967b48ae62c15
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07906653B2

Reaction notes

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