Ammonium Hydroxide → HCID 66742363, compound

HRID 1431069Notes

Reaction equation

HRID 1431069 reaction equation
[C:1]([C:3]([C:6]1[CH:14]=[C:13]([CH3:15])[C:9]([C:10](O)=[O:11])=[C:8]([F:16])[CH:7]=1)([CH3:5])[CH3:4])#[N:2].C(N1C=CN=C1)([N:19]1C=CN=C1)=O.[OH-].[NH4+]>O1CCCC1>[C:1]([C:3]([CH3:5])([CH3:4])[C:6]1[CH:14]=[C:13]([CH3:15])[C:9]([C:10]([NH2:19])=[O:11])=[C:8]([F:16])[CH:7]=1)#[N:2]

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 66742474HCID 66742474, compound

Product 1

HCID 66742363HCID 66742363, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(2-cyanopropan-2-yl)-2-fluoro-6-methylbenzoic acid (14 g, 35 mmol, 75% pure) was taken up in dry tetrahydrofuran (100 ml). To this was added 1,1′-carbonyldiimidazole (11.2 g, 69.1 mmol) in four equal portions over 15 minutes. The mixture was stirred for 2.5 hours and then a 28% aqueous solution of ammonium hydroxide (20.4 ml) was added via drop-wise addition. The material was stirred for 4 hours and then concentrated under reduced pressure to remove 90% of the volatiles. The residue was taken up in water (80 ml) and dichloromethane (80 ml) and shaken in a reparatory funnel. The organic phase was collected and the aqueous phase was back extracted with dichloromethane (3×60 ml). The combined organic phase was dried (magnesium sulfate), filtered and concentrated in vacuo and the resultant semisolid was purified via trituration from hot dichloromethane/hexanes to provide the desired product as a slightly-impure off-white solid (10.71 g, 80% purity). (M+H)+=221 m/e.

Workup

  1. stirringThe material was stirred for 4 hours
  2. concentrationconcentrated under reduced pressure
  3. customto remove 90% of the volatiles
  4. stirringdichloromethane (80 ml) and shaken in a reparatory funnel
  5. customThe organic phase was collected
  6. extractionthe aqueous phase was back extracted with dichloromethane (3×60 ml)
  7. dry with materialThe combined organic phase was dried (magnesium sulfate)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customthe resultant semisolid was purified via trituration from hot dichloromethane/hexanes

Sources & evidence

ORD record
ord-5f3dc39728dd475f88eb2d771d5c272a
Source dataset
uspto-grants-2015_01
Patent number
US08940741B2

Reaction notes

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