Ammonium Chloride → HCID 178492477, compound

HRID 1611846Notes

Reaction equation

HRID 1611846 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:21][C:22]#[N:23])[CH:5]=[C:6]([Cl:20])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([CH:17]([CH3:19])[CH3:18])[CH:10]=1.[Cl-].[NH4+].[N-:26]=[N+:27]=[N-:28].[Na+]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([Cl:20])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([CH:17]([CH3:19])[CH3:18])[CH:10]=1)[CH2:21][C:22]1[NH:28][N:27]=[N:26][N:23]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 22255817HCID 22255817, compound

Product 1

HCID 178492477HCID 178492477, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 3,5-dichloro-4-(4-methoxy-3-isopropylphenoxy)-phenylacetonitrile (160 mg) in 3.0 ml of dimethyl formamide, ammonium chloride (500 mg) and sodium azide (600 mg) was added at reflux. After 2 hours the reaction mixture was concentrated, treated with 6 M hydrochloric acid and extracted several times with ethyl acetate. The combined organic phases were dried over magnesium sulphate, filtered and concentrated. The residue was purified by column chromatography (silica gel, 96:4:1 chloroform/methanol/acetic acid) to give 60 mg (34%) of 3,5-dichloro-4-(4-methoxy-3-isopropylphenoxy)benzyltetrazole.

Workup

  1. temperatureat reflux
  2. concentrationAfter 2 hours the reaction mixture was concentrated
  3. additiontreated with 6 M hydrochloric acid
  4. extractionextracted several times with ethyl acetate
  5. dry with materialThe combined organic phases were dried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography (silica gel, 96:4:1 chloroform/methanol/acetic acid)

Sources & evidence

ORD record
ord-b77d3619d5444230992783917f226709
Source dataset
uspto-grants-2006_01
Patent number
US06989402B1

Reaction notes

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