Toluene → 4'-((2-Butyl-4-oxo-1,3-diazaspiro(4.4)non-1-ene-3-yl)methyl)(1,1'-biphenyl)-2-carbonitrile

HRID 2425508Notes

Reaction equation

HRID 2425508 reaction equation
[CH2:1]([C:5]1[NH:9][C:8](=[O:10])[C:7]2([CH2:14][CH2:13][CH2:12][CH2:11]2)[N:6]=1)[CH2:2][CH2:3][CH3:4].C1(C)C=CC=CC=1.C[O-].[Na+].Br[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[C:39]#[N:40])=[CH:29][CH:28]=1>C(O)(C)C.O.CN(C=O)C>[CH2:1]([C:5]1[N:9]([CH2:26][C:27]2[CH:28]=[CH:29][C:30]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[C:39]#[N:40])=[CH:31][CH:32]=2)[C:8](=[O:10])[C:7]2([CH2:14][CH2:13][CH2:12][CH2:11]2)[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

8

Reactant 4

HCID 1140TolueneHCID 15019124'-(Bromomethyl)-2-cyanobiphenylHCID 101765112-Butyl-1,3-diazaspiro[4.4]non-1-en-4-oneHCID 10942334Sodium Methoxide

Product 1

HCID 98431164'-((2-Butyl-4-oxo-1,3-diazaspiro(4.4)non-1-ene-3-yl)methyl)(1,1'-biphenyl)-2-carbonitrile

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3776IsopropanolSolventHCID 6228DimethylformamideSolvent

Procedure

A RB flask was charged with 2-(n-butyl)-1,3-diazaspiro[4,4]non-1-ene-4-one (7.0 g), toluene (70 ml), DMF (30 ml) and sodium methoxide (2.2 g) at room temperature and stirred for 15 min, followed by the addition of 4-(bromomethyl)-2′-cyanobiphenyl (10 g). The reaction mixture was stirred for 1 hour and then quenched by the addition of water (100 ml). The layers were separated and organic layer was evaporated to get oily residue. The obtained residue was taken in isopropyl alcohol (10 ml) and water (10 ml) and stirred at room temperature to get solid material. The solid material was filtered and washed with IPA and water mixture and then dried under vacuum.

Workup

  1. stirringThe reaction mixture was stirred for 1 hour
  2. customquenched by the addition of water (100 ml)
  3. customThe layers were separated
  4. customorganic layer was evaporated
  5. customto get oily residue
  6. customto get solid material
  7. filtrationThe solid material was filtered
  8. washwashed with IPA and water mixture
  9. customdried under vacuum

Sources & evidence

ORD record
ord-0d1419e0a34c40bc8e8645ddab8c25d7
Source dataset
uspto-grants-2011_06
Patent number
US07964737B2

Reaction notes

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