Dimethylformamide → HCID 86757984, compound

HRID 843657Notes

Reaction equation

HRID 843657 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].CN(C)C=O.Cl.[CH2:13]([N:16]([CH:20]=[C:21]1[CH:29]=[CH:28]C(C(O)=O)=[CH:23][CH2:22]1)[CH2:17][CH2:18][CH3:19])[CH2:14][CH3:15]>ClCCl>[CH2:17]([N:16]([CH:20]=[C:21]1[CH:22]=[CH:23][C:1]([C:2]([Cl:4])=[O:3])=[CH:28][CH2:29]1)[CH2:13][CH2:14][CH3:15])[CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 86757985HCID 86757985, compound

Product 1

HCID 86757984HCID 86757984, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.283 cm3 of oxalyl chloride and then a drop of dimethylformamide are successively added, at a temperature close to 20° C., to a suspension of 0.748 g of 4-(N,N-di-n-propylaminomethylene)benzoic acid monohydrochloride in 20 cm3 of dichloromethane. The reaction medium is kept stirred at a temperature close to 20° C. until the gaseous emission ceases, and then concentrated to dryness under reduced pressure (about 0.5 kPa) at a temperature close to 35° C. The white solid thus obtained is used as a base for the preparation of 4,4′-O,O-di(4-(N,N-di-n-propylaminomethylene)benzoyl)-2-[(1R,2S,3R)(1,2,3,4-tetrahydroxybutyl)]-5-[(2′S, 3′R)(2′,3′,4′-trihydroxybutyl)]pyrazine.

Workup

  1. customclose to 20° C. until the gaseous emission ceases
  2. concentrationconcentrated to dryness under reduced pressure (about 0.5 kPa) at a temperature
  3. customclose to 35° C
  4. customThe white solid thus obtained

Sources & evidence

ORD record
ord-3cf12857fa714794a4a6f1edbc4cd7a9
Source dataset
uspto-grants-2002_04
Patent number
US06380197B1

Reaction notes

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