Ammonia → HCID 13019464, compound

HRID 2285735Notes

Reaction equation

HRID 2285735 reaction equation
[CH3:1][N:2]([CH3:26])[CH2:3]/[CH:4]=[C:5](/[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1)\[C:6]1[NH:7][CH:8]=[C:9](CC2C=CC=CC=2)[N:10]=1.N.[Na].[Cl-].[NH4+]>C1(C)C=CC=CC=1>[CH3:26][N:2]([CH3:1])[CH2:3][CH2:4][CH:5]([C:18]1[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=1)[C:6]1[NH:10][CH:9]=[CH:8][N:7]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 178490148HCID 178490148, compound

Product 1

HCID 13019464HCID 13019464, compoundYield 89.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of (E) and (Z)-N,N-dimethyl-3-(4-methoxyphenyl)-3-[(1-phenylmethyl)imidazol-2-yl]-2-propen-1-amine (1.0 g) in dry toluene (20 ml) was added to liquid ammonia (20 ml) with stirring at -78°. Sodium was added until the mixture was deep blue (ca. 0.23 g required). After stirring at -78° for 2 h. ammonium chloride (1 g) was added, the mixture allowed to warm to room temperature and the residue partitioned between 2 N sodium carbonate (50 ml) and ethyl acetate (3×50 ml). The organic solution was dried (Na2SO4) and concentrated to give the title compound as a white solid (0.67 g) which crystallised from ether with m.p. 131°-133°, ωmax (CHBr3) 3440 (NH), 2770, 2820 (Me2NCH2 --).

Workup

  1. additionwas added
  2. customthe residue partitioned between 2 N sodium carbonate (50 ml) and ethyl acetate (3×50 ml)
  3. dry with materialThe organic solution was dried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3f7b778cdcb9424aa6d9ac28163f3317
Source dataset
uspto-grants-1982_04
Patent number
US04324792

Reaction notes

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