O-p-Chlorophenyl chlorothioformate → 5-{4-[Ethyl-(2-hydroxy-ethyl)-amino]-butoxy}-2,3-dihydro-indole-1-carbothioic acid O-(4-chloro-phenyl)ester

HRID 49502Notes

Reaction equation

HRID 49502 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]([CH2:19][CH3:20])[CH2:16][CH2:17][OH:18])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][C:29](Cl)=[S:30])=[CH:24][CH:23]=1>>[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][C:29]([N:1]2[C:9]3[C:4](=[CH:5][C:6]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]([CH2:19][CH3:20])[CH2:16][CH2:17][OH:18])=[CH:7][CH:8]=3)[CH2:3][CH2:2]2)=[S:30])=[CH:24][CH:23]=1

Participants

3

Reactant 2

HCID 70306O-p-Chlorophenyl chlorothioformateHCID 219665812-{[4-(2,3-Dihydro-1H-indol-5-yloxy)-butyl]-ethyl amino}-ethanol

Product 1

HCID 865870125-{4-[Ethyl-(2-hydroxy-ethyl)-amino]-butoxy}-2,3-dihydro-indole-1-carbothioic acid O-(4-chloro-phenyl)ester

Procedure

In analogy to example 7.8, 2-{[4-(2,3-Dihydro-1H-indol-5-yloxy)-butyl]-ethyl amino}-ethanol and chloro-thioformic acid (4-chloro-phenyl)ester were converted to yield 5-{4-[Ethyl-(2-hydroxy-ethyl)-amino]-butoxy}-2,3-dihydro-indole-1-carbothioic acid O-(4-chloro-phenyl)ester as yellow viscous oil, MS: 449 (MH+, 1Cl).

Sources & evidence

ORD record
ord-741c9458184945d2b8647fcd05a55754
Source dataset
uspto-grants-2004_03
Patent number
US06706751B2

Reaction notes

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