Hydrochloric Acid → HCID 178521408, compound

HRID 1945410Notes

Reaction equation

HRID 1945410 reaction equation
[Cl:1][C:2]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([NH2:8])=[O:7].[N-:14]=[N+:15]=[N-:16].[Na+].Cl.C([N:21]([CH2:24][CH3:25])CC)C.Cl>CN1CCCC1=O.O>[Cl:1][C:2]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([NH:8][C:3]1[CH:2]=[CH:12][CH:11]=[C:25]([C:24]2[NH:21][N:16]=[N:15][N:14]=2)[CH:9]=1)=[O:7]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 74798Acetamide, 2-(2,4-dichlorophenoxy)-

Product 1

HCID 178521408HCID 178521408, compoundYield 142.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of N-(3-cyano-phenyl)-2-(2,4-dichloro-phenoxyacetamide (70.0 mg, 0.22 mmol), sodium azide (42.9 mg, 0.66 mmol) and triethylamine hydrochloride (45.4 mg, 0.33 mmol) in N-methylpyrrolidone (6 ml) (NMP) was stirred at 150° C. under nitrogen overnight. After cooling, the reaction mixture was diluted with water, acidified to PH 1 with 10% v/v hydrochloric acid, and extracted with ethyl acetate. The organic phase was washed with brine, dried (MgSO4 anh), and concentrated. The residue was purified by silica gel flash column chromatography (CH2CH2:MeOH=3:1) to give 2-(2,4-dichloro-phenoxy)-N-[3-(1H-tetrazole-5-yl)-phenyl]-acetamide as a solid (57.2 mg, 71.6% yield).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with brine
  4. dry with materialdried (MgSO4 anh)
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel flash column chromatography (CH2CH2:MeOH=3:1)

Sources & evidence

ORD record
ord-367028f9080043169aca6b6b62d06e43
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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