Hydrochloric Acid → HCID 178521895, compound

HRID 1603901Notes

Reaction equation

HRID 1603901 reaction equation
[O:1]=[C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[C:11]([NH:12][C:13]([C:15]3[CH:16]=[CH:17][C:18]4[O:22][CH:21]([CH2:23][O:24][CH2:25][C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=5)[CH2:20][C:19]=4[CH:32]=3)=[O:14])[C:6]=2[O:5][C:4]([C:33]#[N:34])=[CH:3]1.[N-:35]=[N+:36]=[N-:37].[Na+].[Cl-].[NH4+].Cl>CN(C)C=O>[O:1]=[C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[C:11]([NH:12][C:13]([C:15]3[CH:16]=[CH:17][C:18]4[O:22][CH:21]([CH2:23][O:24][CH2:25][C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=5)[CH2:20][C:19]=4[CH:32]=3)=[O:14])[C:6]=2[O:5][C:4]([C:33]2[NH:37][N:36]=[N:35][N:34]=2)=[CH:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 19606318HCID 19606318, compound

Product 1

HCID 178521895HCID 178521895, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of N-[4-oxo-2-cyano-4H-1-benzopyran-8-yl]-2-benzyloxymethyl-2,3-dihydrobenzofuran-5-carboxamide (300 mg, 0.66 mmol), sodium azide (129 mg, 1.99 mmol), ammonium chloride (107 mg, 1.99 mmol) and dry N,N-dimethylformamide (10 ml) was left under stirring at 100° C. for 1.25 h. After that the mixture, cooled at room temperature, was poured onto a 1M hydrochloric acid solution (10 ml), recovering by filtration the formed precipitate, thereby obtaining 111 mg of the title compound as a white solid with melting point 200-202° C., which was purified by crystallization in methanol:dichloromethane mixtures (68% yield).

Workup

  1. waitwas left
  2. temperatureAfter that the mixture, cooled at room temperature
  3. filtrationrecovering by filtration the formed precipitate

Sources & evidence

ORD record
ord-760c10d482e54cddb623752bb9c40598
Source dataset
uspto-grants-1999_11
Patent number
US05990142

Reaction notes

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