Dimethylformamide → HCID 19907592, compound

HRID 2371516Notes

Reaction equation

HRID 2371516 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH3:10])=[O:8].[OH:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][CH:19]=2)=[CH:14][CH:13]=1.CN(C)C=O.C(=O)([O-])[O-].[K+].[K+]>O>[C:24]([C:21]1[CH:20]=[CH:19][C:18]([C:15]2[CH:16]=[CH:17][C:12]([O:11][CH:6]([CH2:5][CH2:4][CH2:3][CH3:2])[C:7]([O:9][CH3:10])=[O:8])=[CH:13][CH:14]=2)=[CH:23][CH:22]=1)#[N:25]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 1406104'-Hydroxy-4-biphenylcarbonitrileHCID 4170292Methyl 6-Bromohexanoate

Product 1

HCID 19907592HCID 19907592, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

8.80 g (42 mmole) of methyl 6-bromohexanoate, 8.20 g (42 mmole) of 4-hydroxy-4'-cyanobiphenyl, 20 ml dimethyl formamide and 5.8 g (42 mmole) potassium carbonate were placed in a 100 ml flask equipped with a calcium chloride drying tube, and stirred at room temperature for 24 hours, after which time the mixture was poured into water and the suspended solids filtered out and washed with water. The resultant product was dried in a vacuum desiccator for 48 hours to yield 11.50 g (85%) of the ester which was recrystallized from aqueous ethanol to yield a product with a melting point of 80° C.-81° C.

Workup

  1. customequipped with a calcium chloride drying tube
  2. filtrationthe suspended solids filtered out
  3. washwashed with water
  4. dry with materialThe resultant product was dried in a vacuum desiccator for 48 hours

Sources & evidence

ORD record
ord-7fd71e08b3b14cb08e6d192f8c56991c
Source dataset
uspto-grants-1992_03
Patent number
US05093471

Reaction notes

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