Cysteamine → HCID 4364923, compound

HRID 2223989Notes

Reaction equation

HRID 2223989 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Cl)=[CH:5][CH:4]=1.[NH2:11][CH2:12][CH2:13][SH:14]>CO.C[O-].[Na+]>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][S:14][CH2:13][CH2:12][NH2:11])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 6058CysteamineHCID 699934-Methyloxybenzyl chloride

Product 1

HCID 4364923HCID 4364923, compoundYield 95.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 10942334Sodium MethoxideSolvent

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-78c4ce67814f4d8d8a5607fd0038e7e8
Source dataset
uspto-grants-2008_05
Patent number
US07378079B2

Reaction notes

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