Methyl azide → 1-Methyl-5-p-Toluenesulfonyltetrazole

HRID 370526Notes

Reaction equation

HRID 370526 reaction equation
[C:1]1([CH3:12])[CH:6]=[CH:5][C:4]([S:7]([C:10]#[N:11])(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH3:13][N:14]=[N+:15]=[N-:16]>C1C=CC=CC=1>[CH3:13][N:14]1[C:10]([S:7]([C:4]2[CH:3]=[CH:2][C:1]([CH3:12])=[CH:6][CH:5]=2)(=[O:8])=[O:9])=[N:11][N:16]=[N:15]1

Participants

4

Reactant 2

HCID 79079Methyl azideHCID 87946p-Toluenesulphonyl cyanide

Product 1

HCID 135188271-Methyl-5-p-Toluenesulfonyltetrazole

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 36.2 g. (0.2 mol.) of p-toluenesulfonyl cyanide [M. J. Cox and R. Ghosh, Tet. Letters, 3351 (1969)] and 50 g. (0.9 mol.) of methyl azide [O. Dimroth, Ber., 38, 1572 (1905)] in 100 ml. of benzene is heated in a sealed bomb at 80° for 4 hours. The reaction mixture is filtered and allowed to cool to give 42 g. of crystallize product, m.p. 110°-111° C.

Workup

  1. additionA mixture of 36.2 g
  2. filtrationThe reaction mixture is filtered
  3. temperatureto cool
  4. customto give 42 g

Sources & evidence

ORD record
ord-109aff9dbbda421caa3e3925add11795
Source dataset
uspto-grants-1985_07
Patent number
US04526978

Reaction notes

Loading…