Dimethylamine → HCID 67107649, compound

HRID 1623680Notes

Reaction equation

HRID 1623680 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][O:8][C:9]([C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][C:19]=1[O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:14](O)=[O:15])=[O:10].[CH3:28][NH:29][CH3:30].O>ClCCl.CN(C)C=O>[CH3:28][N:29]([CH3:30])[C:14]([C:13]1[CH:17]=[CH:18][C:19]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:11]([CH:12]=1)[C:9]([O:8][CH3:7])=[O:10])=[O:15]

Participants

7

Reactant 4

HCID 674DimethylamineHCID 962WaterHCID 65578Oxalyl chlorideHCID 671067771285516-45-1

Product 1

HCID 67107649HCID 67107649, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Oxalyl chloride (0.46 ml, 5.24 mmol) was added dropwise to a stirred solution of 3-[(methyloxy)carbonyl]-4-[(phenylmethyl)oxy]benzoic acid (may be prepared as described in Description 49; 300 mg, 1.05 mmol) in dichloromethane (10 ml) and dimethylformamide (3 drops) at room temperature. The mixture was stirred at room temperature for 1 h. The solvent was removed, and the residue was dissolved in dichloromethane (5 ml). This mixture was added to a solution of dimethylamine (716 mg, 5.24 mmol) in dichloromethane (5 ml). The mixture was stirred at room temperature for 2 h. Water (40 ml) was added and the mixture was extracted with dichloromethane (3×60 ml). The organic phase was washed with saturated brine (25 ml), dried over sodium sulfate, and evaporated in vacuo to give the crude product as colourless oil. The crude product was used directly in the next step without further purification.

Workup

  1. customThe solvent was removed
  2. dissolutionthe residue was dissolved in dichloromethane (5 ml)
  3. stirringThe mixture was stirred at room temperature for 2 h
  4. extractionthe mixture was extracted with dichloromethane (3×60 ml)
  5. washThe organic phase was washed with saturated brine (25 ml)
  6. dry with materialdried over sodium sulfate
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-d85463a4651649d39b6302c55a5208c7
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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