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

HRID 1723528Notes

Reaction equation

HRID 1723528 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.[NH:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1.Cl>>[N:24]1([CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2/[CH:13]=[CH:14]/[C:15]2[S:16][C:17]3[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=3[N:19]=2)[CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 31268PyrrolidineHCID 20025798HCID 20025798, compound

Product 1

HCID 20025806(E)-2-[2-(4-Pyrrolidinobutoxyphenyl)ethenyl]benzothiazoleYield 33%

Procedure

The title compound was prepared in accordance with Example 38 starting with (H) of Example 38 (3.0 g, 8.7 mmol) and using pyrrolidine in place of dipropylamine to produce 1.1 g (33% yield) of the title compound as the HCl salt, mp 220°-222° C. IR(KBr): 3410, 1600 cm-1. MS: 379(MH+). 1H NMR (CD3OD): δ 8.02-6.91 (m, 10H), 4.12 (t, J=5.2 Hz, 2H), 3.23 (m, 6H), 2.54 (m, 4H), 2.21 (m, 4H).

Sources & evidence

ORD record
ord-f4147da308c24eea947ad7f5f89e5597
Source dataset
uspto-grants-1989_08
Patent number
US04861897

Reaction notes

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