Dimethylformamide → HCID 19764676, compound

HRID 247974Notes

Reaction equation

HRID 247974 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:23][C:24]([OH:26])=O)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].CN(C)C=O.C(Cl)(=O)C([Cl:35])=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:23][C:24]([Cl:35])=[O:26])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 19015033HCID 19015033, compound

Product 1

HCID 19764676HCID 19764676, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 10 g of product from Example 64, 0.095 g of dimethylformamide and 150 ml of methylene chloride is added, dropwise, 3.42 ml of oxalyl chloride. The reaction is stirred at room temperature for 69 hours and then concentrated in vacuo. The residue is dissolved in diethyl ether, filtered and concentrated in vacuo to give 10.5 g of the desired product as a yellow oil.

Workup

  1. additionis added
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue is dissolved in diethyl ether
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e851f393ce23435bbad5ac601a5b5a28
Source dataset
uspto-grants-1993_05
Patent number
US05208247

Reaction notes

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