Methylamine → HCID 18324841, compound

HRID 1250886Notes

Reaction equation

HRID 1250886 reaction equation
CN.[CH2:3]([N:6]1[CH2:11][CH2:10][CH2:9][N:8]([C:12]2[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=2[CH3:19])C1=S)C=C>C(O)C.ClCCl>[Cl:18][C:16]1[CH:15]=[CH:14][C:13]([CH3:19])=[C:12]([NH:8][CH2:9][CH2:10][CH2:11][NH:6][CH3:3])[CH:17]=1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 9925710HCID 9925710, compound

Product 1

HCID 18324841HCID 18324841, compoundYield 84.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To an 8.03 M solution of methylamine in ethanol (27 mL) was added the hydrobromide salt of Example 8, Step B (7.5 g). The reaction was stirred at ambient temperature for 18 hours. The solvent was removed in vacuo and the residue partitioned between dichloromethane and 1N sodium hydroxide. The organic phase was washed with brine, dried over sodium sulfate and concentrated in vacuo to give a brown oil. The crude material was dissolved in dichloromethane and absorbed onto a column of Merck-60 flash silica gel. Elution with a solvent gradient (from 98:2 to 90:10 dichloromethane-methanol containing 0.2% ammonium hydroxide) gave the title compound (3.9 g, 84.1%) as a pale orange oil, which was used as such in the next step.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue partitioned between dichloromethane and 1N sodium hydroxide
  3. washThe organic phase was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto give a brown oil
  7. customabsorbed onto a column of Merck-60 flash silica gel
  8. washElution with a solvent gradient (from 98:2 to 90:10 dichloromethane-methanol containing 0.2% ammonium hydroxide)

Sources & evidence

ORD record
ord-ed4b1ad3befc482e8ed4b60f7855ea6c
Source dataset
uspto-grants-2002_01
Patent number
US06340687B1

Reaction notes

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