2-(4-Hydroxyphenyl)benzothiazole → HCID 20375258, compound

HRID 1448698Notes

Reaction equation

HRID 1448698 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1.Br[CH2:18][CH2:19][O:20][CH:21]1[CH2:26][C:25]([CH3:28])([CH3:27])[NH:24][C:23]([CH3:30])([CH3:29])[CH2:22]1>>[S:9]1[C:10]2[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=2[N:12]=[C:8]1[C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:18][CH2:19][O:20][CH:21]2[CH2:22][C:23]([CH3:30])([CH3:29])[NH:24][C:25]([CH3:27])([CH3:28])[CH2:26]2)=[CH:7][CH:6]=1

Participants

3

Reactant 2

HCID 957452-(4-Hydroxyphenyl)benzothiazoleHCID 203752634-(2-Bromoethoxy)-2,2,6,6-tetramethylpiperidine

Product 1

HCID 20375258HCID 20375258, compound

Procedure

A hot solution of 16 g. of zinc, o-aminophenylmercaptide and 12.5 g. of p-hydroxybenzaldehyde in 1 l. of acetic acid was treated with hydrogen sulfide for two hours, filtered hot, diluted with an equal volume of water and cooled. 2-(p-Hydroxyphenyl)benzothiazole (47% yield, m.p. 227°-229° F.) was obtained. The 2-(p-hydroxyphenyl)benzothiazole was reacted with 4-(2-bromoethoxy)-2,2,6,6-tetramethylpiperidine as in Example 1 to produce 4-{2-[4-(2-benzothiazolyl)phenoxy]ethoxy}-2,2,6,6-tetramethylpiperidine.

Sources & evidence

ORD record
ord-0e0c97abf01a4ebda48f6c2391de1dfe
Source dataset
uspto-grants-1980_02
Patent number
US04187213

Reaction notes

Loading…