HCID 21138071, compound → HCID 59716021, compound

HRID 2223990Notes

Reaction equation

HRID 2223990 reaction equation
Cl[CH2:2][C:3]([NH:5][CH2:6][CH2:7][S:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1)=[O:4]>C(#N)C>[CH3:17][O:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][S:8][CH2:7][CH2:6][NH:5][C:3](=[O:4])[CH2:2][NH:5][CH2:6][CH2:7][S:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[CH:11][CH:12]=1

Participants

3

Reactant 1

HCID 21138071HCID 21138071, compound

Product 1

HCID 59716021HCID 59716021, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Methoxybenzyl chloride (15.6 g) was reacted with 2-aminoethanethiol (7.7 g) in methanol and sodium methoxide, to afford of 2-(4-methoxybezyl-sulfanyl)-ethylamine (1) (18.8 g). One half of this material was taken in dichloromethane (cooling bath 0° C.). Chloroacetyl chloride in the same solvent, was added slowly with stirring, followed by an equivalent of triethyl amine to produce 2-chloro N-[2-(4-methoxybenzyl-sulfanyl)-ethyl]acetamide (2) in a 94% yield. Compound 2 was reacted with an equivalent amount of 1 in refluxing acetonitrile for 6 hrs to provide N-[-2-(4-methoxy-benzylsulfanyl)-ethyl]-2-[2-(4-methoxy-benzylsulfanyl)-ethylamino]-acetamide (3) (40.4 g). Compound 3 was reduced with lithium aluminium hydride (LAH) to yield 4 in 85%.

Sources & evidence

ORD record
ord-02be9a9393304acb80a58d3328d63a72
Source dataset
uspto-grants-2008_05
Patent number
US07378079B2

Reaction notes

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