Methane → HCID 13753969, compound

HRID 979826Notes

Reaction equation

HRID 979826 reaction equation
[CH2:1]([NH2:4])[CH2:2][NH2:3].C[Al](C)C.C.[NH2:10][C:11]1[C:12]([Cl:27])=[C:13]2[C:18](=[C:19]([CH3:22])[C:20]=1[Cl:21])[CH:17]([C:23](OC)=O)[CH2:16][CH2:15][CH2:14]2>C1(C)C(C)=CC=CC=1.CO.O>[ClH:21].[NH2:10][C:11]1[C:12]([Cl:27])=[C:13]2[C:18](=[C:19]([CH3:22])[C:20]=1[Cl:21])[CH:17]([C:23]1[NH:3][CH2:2][CH2:1][N:4]=1)[CH2:16][CH2:15][CH2:14]2

Participants

8

Reactant 4

HCID 297MethaneHCID 3301EthylenediamineHCID 16682925TrimethylaluminumHCID 131715007HCID 131715007, compound

Product 1

HCID 13753969HCID 13753969, compoundYield 56%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 7237O-XyleneSolvent2×

Procedure

Ethylenediamine (0.53 ml) was added dropwise to a stirred solution of trimethyl aluminum (4 ml) in 50 ml xylene at 0° C. under an atmosphere of nitrogen. At the end of methane evolution a solution of the product from Example 136 (0.41 g) in xylene (10 ml) was added. The reaction mixture was refluxed for 24 hours. After cooling, the solution was treated with water (10 ml), methanol (20 ml) and the solvent evaporated to one-half volume. The solution was diluted with water, and extracted with methylene chloride. The organic layer was dried and evaporated and the oily residue was purified by column chromatography affording the desired compound in 56% yield. The solid was dissolved in methanol and ethereal hydrochloric acid, affording the desired hydrochloride salt. m.p. 218°-21° C.

Workup

  1. temperatureThe reaction mixture was refluxed for 24 hours
  2. temperatureAfter cooling
  3. customthe solvent evaporated to one-half volume
  4. additionThe solution was diluted with water
  5. extractionextracted with methylene chloride
  6. customThe organic layer was dried
  7. customevaporated
  8. customthe oily residue was purified by column chromatography

Sources & evidence

ORD record
ord-2c22779c33c04e3f9691e14666ee108c
Source dataset
uspto-grants-1987_01
Patent number
US04634705

Reaction notes

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