Thiourea → (S)-4-(2-methyloxy-3-(1-methyloxyheptyl)phenyl)thiazole-2-amine

HRID 337196Notes

Reaction equation

Cl[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C@@H:11]([O:18][CH3:19])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:6]=1[O:20][CH3:21])=O.[NH2:22][C:23]([NH2:25])=[S:24]>C(O)C>[CH3:21][O:20][C:6]1[C:7]([C@@H:11]([O:18][CH3:19])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:8][CH:9]=[CH:10][C:5]=1[C:3]1[N:22]=[C:23]([NH2:25])[S:24][CH:2]=1

Participants

Conditions

Temperature: 100 °C

Procedure

(S)-2-chloro-1-(2-methyloxy-3-(1-methyloxyheptyl)phenyl)ethanone (11) obtained in the third step was dissolved in ethanol (30 ml,), thiourea (1.4 g) was added, and the mixture was stirred at 100° C. for 3 hours. Extraction with toluene and purification by silica gel chromatography afforded (S)-4-(2-methyloxy-3-(1-methyloxyheptyl)phenyl)thiazole-2-amine (12, 4.22 g, yield 32%).

Workup

extractionExtraction
customwith toluene and purification by silica gel chromatography

Sources & evidence

ORD record: ord-2f806d83bd6c473ca7209d40ba94fb02
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889722B2

Reaction notes

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