Dimethylformamide → HCID 53994381, compound

HRID 2259713Notes

Reaction equation

HRID 2259713 reaction equation
[CH2:1]([O:4][C@H:5]1[C@@H:11]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C@@H:10]([CH2:20][O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[O:9][CH:7](O)[C@@H:6]1[O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH:2]=[CH2:3].CN(C)C=O.C(Cl)(=O)C([Cl:45])=O>ClCCl>[CH2:1]([O:4][C@H:5]1[C@@H:11]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C@@H:10]([CH2:20][O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[O:9][CH:7]([Cl:45])[C@@H:6]1[O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 14504966HCID 14504966, compound

Product 1

HCID 53994381HCID 53994381, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound Y (505 mg, 1.03 mmol) in dry dichloromethane (8 ml) was treated with N,N-dimethylformamide (0.55 ml) and oxalyl chloride (0.55 ml) at room temperature for 45 minutes. The mixture was diluted with ice-cold toluene (40 ml), then quickly washed with ice-cold water (6 ml) and ice-cold, saturated, aqueous sodium hydrogencarbonate (6 ml), dried (Na2SO4) and concentrated to give crude Z in quantitative yield.

Workup

  1. washquickly washed with ice-cold water (6 ml) and ice-cold
  2. dry with materialsaturated, aqueous sodium hydrogencarbonate (6 ml), dried (Na2SO4)
  3. concentrationconcentrated
  4. customto give crude Z in quantitative yield

Sources & evidence

ORD record
ord-2fbe3988ec1f4a4ca9eec777abe3d516
Source dataset
uspto-grants-1995_12
Patent number
US05474986

Reaction notes

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