Dimethylformamide → HCID 22912858, compound

HRID 1899925Notes

Reaction equation

HRID 1899925 reaction equation
[Cl:1][C:2]1[C:7]([NH:8][C:9]([CH3:14])([C:11]([OH:13])=[O:12])[CH3:10])=[C:6]([N+:15]([O-:17])=[O:16])[CH:5]=[CH:4][CH:3]=1.[CH3:18]N(C=O)C.C(=O)([O-])[O-].[K+].[K+].IC>O>[CH3:18][O:12][C:11](=[O:13])[C:9]([CH3:10])([CH3:14])[NH:8][C:7]1[C:2]([Cl:1])=[CH:3][CH:4]=[CH:5][C:6]=1[N+:15]([O-:17])=[O:16]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 22912940HCID 22912940, compound

Product 1

HCID 22912858HCID 22912858, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of N-(6-chloro-2-nitrophenyl)-2-methylalanine (X, EXAMPLE 14, 11.4 g), DMF (130 ml), potassium carbonate (18.2 g) and iodomethane (13.8 ml) is stirred at 20°-25° for 16 hr, diluted with water, extracted several times with ether. The ether phases are combined and are washed with water and saline, dried over magnesium sulfate and concentrated to give the title compound, IR (mineral oil) 3369, 2990, 2951, 1738, 1598, 1534, 1492, 1451, 1386, 1337, 1277, 1188, 1145, 1103 and 749 cm-1 ; NMR (CDCl3) 7.97, 7.55, 6.94, 6.89, 3.78 and 1.53 δ; MS (m/z) 272 and 213.

Workup

  1. extractionextracted several times with ether
  2. washare washed with water and saline
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0d6512aa246a442580049962de2aff50
Source dataset
uspto-grants-1996_11
Patent number
US05574038

Reaction notes

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