Hydrochloric Acid → HCID 178515925, compound

HRID 1005971Notes

Reaction equation

HRID 1005971 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)#[N:2].[N-:10]=[N+:11]=[N-:12].[Na+].Cl.C(N(CC)CC)C.Cl>CN1CCCC1=O>[OH:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]2[NH:12][N:11]=[N:10][N:2]=2)=[CH:4][CH:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11130Triethylamine hydrochlorideHCID 130194-CyanophenolHCID 33557Sodium Azide

Product 1

HCID 178515925HCID 178515925, compoundYield 78.6%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 4-cyanophenol (4.8 g, 40 mmol), sodium azide (7.8 g, 120 mmol) and triethylamine hydrochloride (8.24 g, 60 mmol) in 1-methyl-2-pyrrolidinone (40 ml) was stirred and heated in an oil bath at 140° C. for five hours. The cooled solution was acidified with 2M hydrochloric acid (200 ml) and extracted with ethyl acetate (3×100 ml). The combined ethyl acetate extracts were washed with water (3×100 ml), dried over anhydrous magnesium sulphate, filtered and evaporated to a fawn solid which was crystallised from 50% v/v ethyl acetate in isohexane to give the title compound (5.1 g.) NMR d (d6-DMSO) 6.95 (2H,d), 7.85 (2H,d), 10.13 (1H,br); MS[MH]+ 163

Workup

  1. extractionextracted with ethyl acetate (3×100 ml)
  2. washThe combined ethyl acetate extracts were washed with water (3×100 ml)
  3. dry with materialdried over anhydrous magnesium sulphate
  4. filtrationfiltered
  5. customevaporated to a fawn solid which
  6. customwas crystallised from 50% v/v ethyl acetate in isohexane

Sources & evidence

ORD record
ord-279d841d85d94ce5ac93cb16800d9690
Source dataset
uspto-grants-2004_09
Patent number
US06787556B1

Reaction notes

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