Ammonium Chloride → HCID 70533072, compound

HRID 435450Notes

Reaction equation

HRID 435450 reaction equation
[CH3:1][Si:2]([CH3:15])([CH3:14])[C:3]#[C:4][CH2:5][N:6]=[CH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C([Li])CCC.[C:21]1([C:27]2[C:28]3[O:33][CH2:32][O:31][CH:30](Cl)[C:29]=3[CH:35]=[CH:36][C:37]=2[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[NH4+].[Cl-]>O.O1CCCC1>[C:21]1([C:27]2[C:28]3[O:33][CH2:32][O:31][CH:30]([CH:5]([N:6]=[CH:7][C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=4)[C:4]#[C:3][Si:2]([CH3:14])([CH3:1])[CH3:15])[C:29]=3[CH:35]=[CH:36][C:37]=2[C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 12918300HCID 12918300, compoundHCID 70533310HCID 70533310, compoundHCID 178418339Butyllithium

Product 1

HCID 70533072HCID 70533072, compoundYield 109.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 1-trimethylsilyl-N-benzylidene-3-aminoprop-1-yne (7.609 g.; 34.4 mmol) in 106 ml. of tetrahydrofuran maintained at -78° under N2 was added dropwise 19.5 ml. of 1.63 N n-butyl lithium. To the stirred deep red solution was then added dropwise 11.43 g. (35.4 mmol) of 3,4-diphenylmethylenedioxybenzyl chloride in 35 ml. of tetrahydrofuran. After an additional 30 minutes at -78° water (25 ml.) was added dropwise, the mixture was warmed to 20°, 10% aqueous NH4Cl solution was added and the layers were separated. The aqueous layer was washed twice with benzene, the combined organic phases were washed twice with cold 10% aqueous NH4Cl, once with saturated NaCl solution, dried over Na2SO4 and concentrated to dryness to give 3-(3,4-diphenylmethylenedioxybenzyl)-1-trimethylsilyl-N-benzylidene-3-aminoprop-1-yne as a viscous orange oil (18,86 g).

Workup

  1. additionwas added dropwise 19.5 ml
  2. additionTo the stirred deep red solution was then added dropwise 11.43 g
  3. temperaturethe mixture was warmed to 20°
  4. customthe layers were separated
  5. washThe aqueous layer was washed twice with benzene
  6. washthe combined organic phases were washed twice with cold 10% aqueous NH4Cl, once with saturated NaCl solution
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-84b54e3d7ee84c409d5e70fbfe640e14
Source dataset
uspto-grants-1983_08
Patent number
US04401676

Reaction notes

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