Benzaldehyde, 4-hexyl- → HCID 18435227, compound
Reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[CH:5]=[CH:4][C:3]=1[SH:10].[CH2:11]([C:17]1[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]>>[F:8][C:7]1[C:2]2[N:1]=[C:21]([C:20]3[CH:23]=[CH:24][C:17]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[CH:18][CH:19]=3)[S:10][C:3]=2[CH:4]=[CH:5][C:6]=1[F:9]Participants
3
Procedure
2-Amino-3,4-difluorothiophenol [131105-92-5] is reacted analogously to Reference 1 with 4-hexylbenzaldehyde (commercially available, [49763-69-1]) to give 4,5-difluoro-2-(4-hexylphenyl)benzothiazoline, which is converted into 4,5-difluoro-2-(4-hexylphenyl)benzothiazole using barium permanganate by the method described in the cited literature. a-Lithiation (by means of lithium diisopropylamide analogously to J. Chem. Soc. Perkin Trans. II 1989, 2048) and quenching with hexyl bromide gives the target compound, which can be purified by chromatography and by recrystallization from acetonitrile.
Sources & evidence
- ORD record
- ord-3475607acc5d4e5ba6e4d17fb30b336b
- Source dataset
- uspto-grants-2002_08
- Patent number
- US06436489B1
Reaction notes
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