Dimethylformamide → HCID 19775327, compound

HRID 1613180Notes

Reaction equation

HRID 1613180 reaction equation
C(Cl)(=O)C([Cl:4])=O.Cl.[C:8]([C:11]1[CH:37]=[CH:36][C:14]([CH2:15][N:16]([C:18]([CH3:35])([CH3:34])[CH2:19][O:20][CH:21]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH3:17])=[CH:13][CH:12]=1)(O)=[O:9].C[N:39](C)C=O>C(Cl)Cl>[ClH:4].[C:8]([C:11]1[CH:37]=[CH:36][C:14]([CH2:15][N:16]([C:18]([CH3:35])([CH3:34])[CH2:19][O:20][CH:21]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH3:17])=[CH:13][CH:12]=1)(=[O:9])[NH2:39]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 19775333HCID 19775333, compound

Product 1

HCID 19775327HCID 19775327, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneCatalyst

Procedure

Oxalyl chloride (200 μl) was added to a solution of 2-[N-(4-carboxybenzyl)-N-methylamino]-1-diphenylmethoxy-2-methylpropane hydrochloride (300 mg -- see Example 43) in methylene chloride containing two drops of dimethylformamide and the mixture was stirred at room temperature for 30 minutes. Ammonia was then bubbled through the stirred solution for 30 minutes which was then diluted with methylene chloride, washed with 10% aqueous sodium hydroxide solution, dried over magnesium sulphate and evaporated. The residue was dissolved in ether and the solution was treated with excess saturated ethereal hydrogen chloride. The resulting precipitated oil was collected, washed with ether and dried to give the title compound as a colourless foam which was characterised as containing 0.75 molar equivalents of water (63 mg, 23%).

Workup

  1. customAmmonia was then bubbled through the stirred solution for 30 minutes which
  2. additionwas then diluted with methylene chloride
  3. washwashed with 10% aqueous sodium hydroxide solution
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. dissolutionThe residue was dissolved in ether
  7. additionthe solution was treated with excess saturated ethereal hydrogen chloride
  8. customThe resulting precipitated oil
  9. customwas collected
  10. washwashed with ether
  11. customdried

Sources & evidence

ORD record
ord-79ac31963ae643e4bc3f70ffa5ee929f
Source dataset
uspto-grants-1993_03
Patent number
US05192765

Reaction notes

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