Ammonium Chloride → HCID 178424087, compound

HRID 1182433Notes

Reaction equation

HRID 1182433 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:20][C:21]#[N:22])[CH:5]=[C:6]([CH3:19])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([CH:16]([CH3:18])[CH3:17])[CH:10]=1.[Cl-].[NH4+].[N-:25]=[N+:26]=[N-:27].[Na+]>CN(C)C=O>[CH3:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([CH3:19])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([CH:16]([CH3:18])[CH3:17])[CH:10]=1)[CH2:20][C:21]1[NH:27][N:26]=[N:25][N:22]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 22255825HCID 22255825, compound

Product 1

HCID 178424087HCID 178424087, compoundYield 38.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 3,5-dimethyl-4-(4-hydroxy-3-isopropylphenoxy)-phenylacetonitrile (154 mg) in 6.3 ml of dimethyl formamide, ammonium chloride (297 mg, 5.21 mmol) and sodium azide (339 mg, 5.21 mmol) was added at reflux. After 4.5 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 68 mg (37%) of the title compound.

Workup

  1. temperatureat reflux
  2. concentrationAfter 4.5 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-dc6ef47f46274aecab31acd43b10333f
Source dataset
uspto-grants-2007_10
Patent number
US07288571B2

Reaction notes

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