Water → HCID 19980332, compound

HRID 1461262Notes

Reaction equation

HRID 1461262 reaction equation
[NH2:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][N:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]3[CH:17]=[N:18][C:19]([C:20]4[N:24]=[C:23]([CH:25]5[CH2:27][CH2:26]5)[O:22][N:21]=4)=[C:9]3[C:8]2=[O:28])=[CH:4][CH:3]=1.N([O-])=O.[Na+].[N-:35]=[N+:36]=[N-].[Na+].O>FC(F)(F)C(O)=O>[N:1]([C:2]1[CH:30]=[CH:29][C:5]([CH2:6][N:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]3[CH:17]=[N:18][C:19]([C:20]4[N:24]=[C:23]([CH:25]5[CH2:27][CH2:26]5)[O:22][N:21]=4)=[C:9]3[C:8]2=[O:28])=[CH:4][CH:3]=1)=[N+:35]=[N-:36]

Participants

6

Reactant 4

HCID 962WaterHCID 33557Sodium AzideHCID 19980275HCID 19980275, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 19980332HCID 19980332, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a stirred solution of 5-(4-aminobenzyl)-3-(5-cyclopropyl-1,2,4-oxadiazol-3-yl)-4,5-dihydro-4-oxo-imidazo[1,5-a]quinoxaline (0.1 g, 0.25 mmol) in trifluoroacetic acid (3 ml) at 0° C. was added sodium nitrite (0.1 g, 1.4 mmol). After 5 min. sodium azide (0.16 g, 2.5 mmol) was added. Stirring was continued for 1 h. Then water (20 ml) was added, and the mixture was extracted twice with dichloromethane (20 ml). The combined extracts were dried over sodium sulphate and evaporated to give the title compound as a pale yellow solid, m.p. 183°-184° C. (dec.). Chromatographic purification (SiO2)/CH2Cl2 -acetone 4:1) gave crystals with m.p. 194°-197° C. (dec.).

Workup

  1. extractionthe mixture was extracted twice with dichloromethane (20 ml)
  2. dry with materialThe combined extracts were dried over sodium sulphate
  3. customevaporated

Sources & evidence

ORD record
ord-8a7ac7483aa0494e9a63294c446bf643
Source dataset
uspto-grants-1991_12
Patent number
US05075304

Reaction notes

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