Ammonium Chloride → HCID 178422379, compound

HRID 1447734Notes

Reaction equation

HRID 1447734 reaction equation
[CH3:1][C:2]1[C:3](=[O:18])[C:4]2[CH2:13][S:12][C:11]3[CH:14]=[CH:15][CH:16]=[CH:17][C:10]=3[C:5]=2[O:6][C:7]=1[C:8]#[N:9].[N-:19]=[N+:20]=[N-:21].[Na+].[Cl-].[NH4+]>CN(C)C=O>[CH3:1][C:2]1[C:3](=[O:18])[C:4]2[CH2:13][S:12][C:11]3[CH:14]=[CH:15][CH:16]=[CH:17][C:10]=3[C:5]=2[O:6][C:7]=1[C:8]1[NH:21][N:20]=[N:19][N:9]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 12561496HCID 12561496, compound

Product 1

HCID 178422379HCID 178422379, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 3-methyl-4-oxo-4H,5H-[1]benzothiopyrano[4,3-b]pyran-2-carbonitrile (3.14 g, 12.3 mmoles, described in Example 6), sodium azide (0.884 g, 13.6 mmoles) and ammonium chloride (0.130 g, 2.4 mmoles) in dimethylformamide (18 ml) is heated at 110° C. for 18 hr. The dark solution is evaporated and the residue is dissolved in water (50 ml). The aqueous solution is washed with ethyl acetate and acidified with 10% hydrochloric acid. The precipitate is collected, washed with water and crystallized from acetone-water to give the title compound (2.5 g), mp 247°-248° C.

Workup

  1. customThe dark solution is evaporated
  2. dissolutionthe residue is dissolved in water (50 ml)
  3. washThe aqueous solution is washed with ethyl acetate
  4. customThe precipitate is collected
  5. washwashed with water
  6. customcrystallized from acetone-water

Sources & evidence

ORD record
ord-c363d2e8e4cc4d728d0019ee4636c888
Source dataset
uspto-grants-1979_12
Patent number
US04177284

Reaction notes

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