Ammonium Chloride → HCID 178420041, compound

HRID 1755887Notes

Reaction equation

HRID 1755887 reaction equation
[C:1]1([C:7]2([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[O:11][C:10]3[CH:12]=[CH:13][C:14]([C:16]#[N:17])=[CH:15][C:9]=3[O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl-].[NH4+].[N-:26]=[N+:27]=[N-:28].[Na+]>>[C:18]1([C:7]2([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[O:11][C:10]3[CH:12]=[CH:13][C:14]([C:16]4[NH:28][N:27]=[N:26][N:17]=4)=[CH:15][C:9]=3[O:8]2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 19917950HCID 19917950, compound

Product 1

HCID 178420041HCID 178420041, compoundYield 70.1%

Procedure

2,2-Diphenyl-1,3-benzodioxol-5-carbonitrile (4.79 g) are heated at 160° C. for 5 hours with 1.71 g of ammonium chloride and 2.08 g of sodium azide. The reaction mixture is cooled to room temperature and partitioned at pH 3 between water and ethyl acetate. The organic phase is shaken with water and the pH value is adjusted to 10 with 1N aqueous sodium hydroxide solution. The aqueous phase (pH 10) is separated, shaken with ethyl acetate and the pH value is adjusted to 4. A white precipitate forms. This is filtered off, dried and recrystallized from 240 ml of acetonitrile. There are obtained 3.84 g of 5-(2,2-diphenyl-1,3-benzodioxol-5-yl)-1H-tetrazole as white crystals of melting point 212°-215° C./dec.

Workup

  1. custompartitioned at pH 3 between water and ethyl acetate
  2. customThe aqueous phase (pH 10) is separated
  3. stirringshaken with ethyl acetate
  4. filtrationThis is filtered off
  5. customdried
  6. customrecrystallized from 240 ml of acetonitrile

Sources & evidence

ORD record
ord-f2204b45756d4a909bf3db37e4be51d4
Source dataset
uspto-grants-1995_08
Patent number
US05438052

Reaction notes

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