Sodium Azide → Methyl 2-azido-3-(benzylsulfanyl)propanoate

HRID 1248265Notes

Reaction equation

HRID 1248265 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH:4](Cl)[CH2:5][S:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[N-:16]=[N+:17]=[N-:18].[Na+]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].O>[CH3:1][O:2][C:3](=[O:15])[CH:4]([N:16]=[N+:17]=[N-:18])[CH2:5][S:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 14189833Methyl 3-(benzylsulfanyl)-2-chloropropanoate

Product 1

HCID 14189838Methyl 2-azido-3-(benzylsulfanyl)propanoateYield 99%

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

15.0 grams (61.3 mmoles) of the 2-chloro-3-benzylmercapto-propionic acid methyl ester produced in Example 3 were stirred with 5.98 grams (92.0 mmoles) of sodium azide and 1.5 grams of Aliquat 336 in 30 ml of water for 7 hours at 45° C. After working up according to Example 2 there were obtained 15.2 grams (99% of theory) of 2-azido-3-benzylmercapto-propionic acid methyl ester.

Sources & evidence

ORD record
ord-cab2bd96767a48038684fa5ac44bdcce
Source dataset
uspto-grants-1985_06
Patent number
US04523012

Reaction notes

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