Dimethylformamide → HCID 67540869, compound

HRID 2196777Notes

Reaction equation

HRID 2196777 reaction equation
COC1C=CC(C(C2C=CC(OC)=CC=2)[N:10]2[C:14]3[CH:15]=[CH:16][CH:17]=[C:18]([O:19][C:20]4[CH:29]=[C:28]([N:30]5[CH2:35][CH2:34][N:33]([CH2:36][C:37]6[CH2:42][CH2:41][C:40]([CH3:44])([CH3:43])[CH2:39][C:38]=6[C:45]6[CH:50]=[CH:49][C:48]([Cl:51])=[CH:47][CH:46]=6)[CH2:32][CH2:31]5)[CH:27]=[CH:26][C:21]=4C(OC)=O)C=3N=C2)=CC=1.[CH3:60][N:61]([CH3:64])[CH:62]=[O:63].C(Cl)(=O)C(Cl)=O>ClCCl>[Cl:51][C:48]1[CH:47]=[CH:46][C:45]([C:38]2[CH2:39][C:40]([CH3:44])([CH3:43])[CH2:41][CH2:42][C:37]=2[CH2:36][N:33]2[CH2:32][CH2:31][N:30]([C:28]3[CH:27]=[CH:26][C:21]4[C:62](=[O:63])[N:61]5[CH:64]=[N:10][C:14]6[CH:15]=[CH:16][CH:17]=[C:18]([C:60]=65)[O:19][C:20]=4[CH:29]=3)[CH2:35][CH2:34]2)=[CH:50][CH:49]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 67539740HCID 67539740, compound

Product 1

HCID 67540869HCID 67540869, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of EXAMPLE 44G (4.5 g) in anhydrous dichloromethane (100 ml) was cooled in an ice bath and catalytic N,N-dimethylformamide was added. This was followed by the dropwise addition of a solution of oxalyl dichloride (1.231 ml) in anhydrous methylene chloride (5 ml). The ice bath was removed and the reaction stirred for 1 hour. The reaction was quenched by the addition of ice (ca. 150 ml) and saturated sodium bicarbonate solution (100 ml). The mixture further diluted with saturated aqueous sodium bicarbonate solution (200 ml) and methylene chloride (200 ml). The crude product was isolated by concentration of the organic layer and the residue was purified on silica gel, eluting with a 0, 10, 25, 100% ethyl acetate in methylene chloride step gradient.

Workup

  1. customThe ice bath was removed
  2. customThe reaction was quenched by the addition of ice (ca. 150 ml) and saturated sodium bicarbonate solution (100 ml)
  3. additionThe mixture further diluted with saturated aqueous sodium bicarbonate solution (200 ml) and methylene chloride (200 ml)

Sources & evidence

ORD record
ord-c298214dd79242988f1c902e4c61bcc7
Source dataset
uspto-grants-2012_12
Patent number
US08338466B2

Reaction notes

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