Triethylamine → (3,5-Dinitrobenzyl)phenylmercaptotetrazole

HRID 66921Notes

Reaction equation

HRID 66921 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[CH2:7]Cl)([O-:3])=[O:2].[C:15]1([S:21][C:22]2[NH:26][N:25]=[N:24][N:23]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C>O1CCCC1.O>[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[CH2:7][N:26]1[C:22]([S:21][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:23][N:24]=[N:25]1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 94673Benzene, 1-(chloromethyl)-3,5-dinitro-HCID 178420563HCID 178420563, compound

Product 1

HCID 86738523(3,5-Dinitrobenzyl)phenylmercaptotetrazoleYield 94.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
10 °C

Procedure

To a solution of 50 g (0.231 mol) of 3,5-dinitrobenzylchloride and 41 g (0.231 mol) of phenylmercaptotetrazole in one liter of dry tetrahydrofuran under nitrogen was added all at once with stirring 23.4 g (0.231 mol) of triethylamine. The temperature rose slowly from 23° to 29°. After stirring overnight the reaction mixture was diluted with one liter of water, cooled to 10° C., filtered and the filter cake was washed well with water. Oven drying at 110° C. for 24 hours gave 78 g (83%) of product mp. 156°-158° C. Recrystallization from tetrahydrofuran gives analytically pure 5, mp. 161.5°-162.5° C.

Workup

  1. customrose slowly from 23° to 29°
  2. filtrationfiltered
  3. washthe filter cake was washed well with water
  4. customOven drying at 110° C. for 24 hours

Sources & evidence

ORD record
ord-9670b2737b6f4ab69907396bc67f9a4c
Source dataset
uspto-grants-1982_08
Patent number
US04343893

Reaction notes

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