Dimethylformamide → HCID 178442728, compound

HRID 2071638Notes

Reaction equation

HRID 2071638 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:6][C:3]=1[C:4]#[N:5].[N-:19]=[N+:20]=[N-:21].[Na+].[Cl-].[NH4+].CN(C)C=O>O>[OH:1][C:2]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:6][C:3]=1[C:4]1[NH:21][N:20]=[N:19][N:5]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 196902232-Hydroxy-5-nonylbenzonitrile

Product 1

HCID 178442728HCID 178442728, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 13.5 parts of 2-hydroxy-5-nonyl benzonitrile, 3.6 parts of sodium azide and 2.95 parts of ammonium chloride, 50 parts of dimethyl formamide and 0.5 parts of water was stirred and boiled for four hours. After cooling the mixture was diluted with water and extracted into chloroform. The chloroform solution was washed with water and with 2 × 200 mls of a 2N solution of sodium hydroxide to extract the product. The aqueous alkaline solution was neutralised with 2N sulphuric acid and re-extracted with chloroform. The extract was washed with water, dried, and evaporated to give 7.1 parts of 5-(2-hydroxy-5-nonylphenyl)tetrazole.

Workup

  1. temperatureAfter cooling the mixture
  2. extractionextracted into chloroform
  3. washThe chloroform solution was washed with water and with 2 × 200 mls of a 2N solution of sodium hydroxide
  4. extractionto extract the product
  5. extractionre-extracted with chloroform
  6. washThe extract was washed with water
  7. customdried
  8. customevaporated

Sources & evidence

ORD record
ord-6cb1343a875a4e5693988caaf05b72c9
Source dataset
uspto-grants-1977_09
Patent number
US04048187

Reaction notes

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