Hydrochloric Acid → (E)-2-[2-(4-Diethylaminobutoxyphenyl)ethenyl]benzothiazole

HRID 1723527Notes

Reaction equation

HRID 1723527 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1/[CH:13]=[CH:14]/[C:15]1[S:16][C:17]2[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=2[N:19]=1.[CH2:24]([NH:26][CH2:27][CH3:28])[CH3:25].Cl>>[CH2:24]([N:26]([CH2:27][CH3:28])[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1/[CH:13]=[CH:14]/[C:15]1[S:16][C:17]2[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=2[N:19]=1)[CH3:25]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 8021DiethylamineHCID 20025798HCID 20025798, compound

Product 1

HCID 20025813(E)-2-[2-(4-Diethylaminobutoxyphenyl)ethenyl]benzothiazoleYield 31%

Procedure

The procedure of Example 38 was followed starting with (H) of Example 38 (3.0 g, 8.7 mmol) and using diethylamine in place of dipropylamine to produce 1.2 g (31% yield) of the title compound as the HCl salt, mp 205°-207° C. IR(KBr): 3400, 1605 cm-1. MS: 381(MH+). 1H NMR (CD3OD): δ 8.14-7.04 (m, 10H), 4.14 (t, J=5.2 Hz, 2H), 3.25 (m, 6H), 1.98 (m, 4H), 1.34 (m, 6H).

Sources & evidence

ORD record
ord-f90a7686bf0b4c5faf1942ea2bb28cd3
Source dataset
uspto-grants-1989_08
Patent number
US04861897

Reaction notes

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