6-Methoxy-2-methylbenzothiazole → HCID 14146367, compound

HRID 1723520Notes

Reaction equation

HRID 1723520 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=O)=[CH:8][CH:7]=1.[CH3:14][O:15][C:16]1[CH:25]=[CH:24][C:19]2[N:20]=[C:21]([CH3:23])[S:22][C:18]=2[CH:17]=1>>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:9](/[CH:10]=[CH:23]/[C:21]2[S:22][C:18]3[CH:17]=[C:16]([O:15][CH3:14])[CH:25]=[CH:24][C:19]=3[N:20]=2)=[CH:8][CH:7]=1

Participants

3

Reactant 2

HCID 762546-Methoxy-2-methylbenzothiazoleHCID 35514794-(3-Chloropropoxy)-benzaldehyde

Product 1

HCID 14146367HCID 14146367, compoundYield 28%

Procedure

The procedure of Example 28 was followed starting with 4-chloropropoxybenzaldehyde (5.0 g, 25 mmol) and using 6-methoxy-2-methylbenzothiazole (4.2 ml, 25 mmol) in place of 2-methylbenzothiazole to give (E)-2-[2-(4-chloropropoxyphenyl)ethenyl]-6-methoxybenzothiazole (2.5 g, 28% yield) as an amber oil. 1H NMR (CDCl3): δ 7.44-6.82 (m, 9H9, 4.21 (t, J=5.3 Hz, 2H), 3.93 (s, 3H), 3.41 (t, J=5.3 Hz, 2H), 2.51 (m, 2H).

Sources & evidence

ORD record
ord-e0679cdb838440e5a9e236999f198c02
Source dataset
uspto-grants-1989_08
Patent number
US04861897

Reaction notes

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