Ammonia → HCID 54298002, compound

HRID 2073394Notes

Reaction equation

HRID 2073394 reaction equation
[CH3:1][C:2]1([CH3:24])[C:6](=[O:7])[O:5][C:4]2[CH:8]=[CH:9][C:10]3[C:15]([C:3]1=2)=[CH:14][C:13]([CH2:16][N:17]1[CH:21]=[N:20][CH:19]=[N:18]1)=[C:12]([C:22]#[N:23])[CH:11]=3.S(=O)(=O)(O)[OH:26].N>>[CH3:1][C:2]1([CH3:24])[C:6](=[O:7])[O:5][C:4]2[CH:8]=[CH:9][C:10]3[C:15]([C:3]1=2)=[CH:14][C:13]([CH2:16][N:17]1[CH:21]=[N:20][CH:19]=[N:18]1)=[C:12]([C:22]([NH2:23])=[O:26])[CH:11]=3

Participants

4

Reactant 3

HCID 222AmmoniaHCID 1118Sulfuric AcidHCID 54516723HCID 54516723, compound

Product 1

HCID 54298002HCID 54298002, compound

Procedure

A solution of 1,2-dihydro-1,1-dimethyl-2-oxo-8-(1H-1,2,4-triazol-1-ylmethyl)naphtho[2,1-b]furan-7-carbonitrile, (0.35 g) and concentrated sulphuric acid (2 ml) was kept at room temperature for 18 h. The mixture was treated with crushed ice and neutralised with concentrated aqueous ammonia, and the mixture was extracted twice with ethyl acetate. The combined extracts were dried and evaporated to dryness under reduced pressure, and the residue was purified by flash chromatography using methanol:dichloromethane, 1:14 v/v, as eluant, to give 1,2-dihydro-1,1-dimethyl-2-oxo-8-(1H-1,2,4-triazol-1-ylmethyl)naphtho[2,1-b]furan-7-carboxamide, m.p. 231°-232° after recrystallisation from a mixture of methanol and ethyl acetate.

Workup

  1. extractionthe mixture was extracted twice with ethyl acetate
  2. customThe combined extracts were dried
  3. customevaporated to dryness under reduced pressure
  4. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-aba89d40a2414223a0f40d7ad4fe73a1
Source dataset
uspto-grants-1990_04
Patent number
US04916148

Reaction notes

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