Sodium Chloride → HCID 14627783, compound

HRID 260605Notes

Reaction equation

HRID 260605 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5]#[N:6].[CH3:7][O:8][C:9]1[CH:25]=[CH:24][C:12]([CH2:13][NH:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)=[CH:11][CH:10]=1.C(N(CC)C(C)C)(C)C.[Cl-].[Na+]>CN(C)C=O.O>[CH3:23][O:22][C:19]1[CH:20]=[CH:21][C:16]([CH2:15][N:14]([CH2:2][CH2:3][CH2:4][C:5]#[N:6])[CH2:13][C:12]2[CH:11]=[CH:10][C:9]([O:8][CH3:7])=[CH:25][CH:24]=2)=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 214124-BromobutyronitrileHCID 81531DiisopropylethylamineHCID 714952Bis(4-methoxybenzyl)amine

Product 1

HCID 14627783HCID 14627783, compoundYield 110.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
110 °C

Procedure

A solution of 4-bromobutyronitrile (14.80 g) in dry dimethylformamide (100 ml) was added dropwise over 15 minutes to a stirred solution of bis-(4-methoxybenzyl)amine (25.73 g) and N,N-diisopropylethylamine (35 ml, 26 g) in dry dimethylformamide (100 ml). The yellow solution was heated under nitrogen at 110° C. for 4 hours and was allowed to cool. The solution was poured onto a mixture of water (400 ml) and saturated aqueous sodium chloride (400 ml) and then extracted with ether (2×200 ml). The extracts were dried (Na2SO4) and concentrated in vacuo to give an oil (35.93 g). The product was chromatographed on silica with eluant diisopropyl ether, and was triturated with cyclohexane to give the title compound (26.00 g), m.p. 56°-58° C.

Workup

  1. temperatureto cool
  2. extractionextracted with ether (2×200 ml)
  3. dry with materialThe extracts were dried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d0c9b37ebdcc4abcb5eb1fa1c4c0c78c
Source dataset
uspto-grants-1996_06
Patent number
US05527955

Reaction notes

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