1-Butanaminium, N,N,N-tributyl-, azide → Ethanethioic acid S-[5-(azidomethyl)tetrahydro-3-thienyl]ester

HRID 54786

Reaction equation

HRID 54786 reaction equation
I[CH2:2][CH:3]1[S:7][CH2:6][CH:5]([S:8][C:9](=[O:11])[CH3:10])[CH2:4]1.[N-:12]=[N+:13]=[N-:14].C([N+](CCCC)(CCCC)CCCC)CCC>C(Cl)Cl>[N:12]([CH2:2][CH:3]1[S:7][CH2:6][CH:5]([S:8][C:9](=[O:11])[CH3:10])[CH2:4]1)=[N+:13]=[N-:14]

Participants

4

Reactant 2

HCID 57432321-Butanaminium, N,N,N-tributyl-, azideHCID 54241013Ethanethioic acid S-[tetrahydro-5-(iodomethyl)-3-thienyl]ester

Product 1

HCID 54464306Ethanethioic acid S-[5-(azidomethyl)tetrahydro-3-thienyl]esterYield 46.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution, under argon, of 0.183 g of product from Example 140 in 1.0 ml of dry methylene chloride is treated with 0.689 g of tetra-n-butyl-ammonium azide. The reaction mixture is stirred vigorously overnight at room temperature. The reaction is concentrated in vacuo and the residue purified by chromatography (silica gel: 0-10% diethyl ether/hexane) to give 0.061 g of the desired product.

Workup

  1. concentrationThe reaction is concentrated in vacuo
  2. customthe residue purified by chromatography (silica gel: 0-10% diethyl ether/hexane)

Sources & evidence

ORD record
ord-898193f0f65f4694bd51481f91ebc822
Source dataset
uspto-grants-1997_04
Patent number
US05623081

Linked notes

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