Ammonium Hydroxide → HCID 69059838, compound

HRID 1295061Notes

Reaction equation

HRID 1295061 reaction equation
C([O:3][C:4]([C:6]1[C:7]2[CH2:8][CH:9]3[CH2:14][CH:10]3[C:11]=2[NH:12][N:13]=1)=O)C.[OH-].[NH4+:16]>O1CCOCC1>[CH2:14]1[CH:9]2[CH2:8][C:7]3[C:6]([C:4]([NH2:16])=[O:3])=[N:13][NH:12][C:11]=3[CH:10]12

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 69059432HCID 69059432, compound

Product 1

HCID 69059838HCID 69059838, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of the ester from Step C (14.2 g, 73.9 mmol) in dioxane (140 mL) was added ammonium hydroxide (28% NH3 in H2O, 750 mL). The mixture was placed in a 1000 mL pyrex bottle and agitated on a shaker plate for 22 h at rt. The mixture was concentrated in vacuo to a total volume of 100 mL at which time a light yellow precipitate was evident. The mixture was filtered and the solid was washed with H2O (2×100 mL). Further drying of the solid in vacuo gave 1a,2,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carboxylic acid amide [HPLC/MS: Discovery® C18 column (5μ, 50×2.1 mm), 5% v/v CH3CN (containing 1% v/v TFA) in H2O (containing 1% v/v TFA) gradient to 99% v/v CH3CN in H2O, 0.75 mL/min, tr=1.09 min, ESI+=164.0 (M+H)] as a white solid.

Workup

  1. concentrationThe mixture was concentrated in vacuo to a total volume of 100 mL at which time a light yellow precipitate
  2. filtrationThe mixture was filtered
  3. washthe solid was washed with H2O (2×100 mL)
  4. customFurther drying of the solid in vacuo

Sources & evidence

ORD record
ord-a7a9111fa5ee437ba5e2ed00eeb9a613
Source dataset
uspto-grants-2007_07
Patent number
US07241792B2

Reaction notes

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