Dimethylformamide → HCID 22225205, compound

HRID 1744804Notes

Reaction equation

HRID 1744804 reaction equation
[CH3:1][C:2]1[C:3]2[CH:23]=[CH:22][C:21](=[O:24])[N:20]([C:25]3[CH:33]=[CH:32][C:28]([C:29](O)=[O:30])=[CH:27][CH:26]=3)[C:4]=2[N:5]=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)[N:7]=1.CN(C=O)C.C(Cl)(=O)C([Cl:42])=O>C(Cl)Cl>[CH3:1][C:2]1[C:3]2[CH:23]=[CH:22][C:21](=[O:24])[N:20]([C:25]3[CH:33]=[CH:32][C:28]([C:29]([Cl:42])=[O:30])=[CH:27][CH:26]=3)[C:4]=2[N:5]=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)[N:7]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 10411034HCID 10411034, compound

Product 1

HCID 22225205HCID 22225205, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 10 (0.215 g; 0.487 mmol) and anhydrous DMF (120 uL) in 8 mL of methylene chloride, oxalyl chloride (0.18 g; 5 mmol) was added dropwise at room temperature and the reaction mixture was stirred for 2 h. Then it was concentrated and the oxalyl chloride carefully removed by distillation to yield compound L (0.217 g; 97%). The compound was used in the next step without further purification.

Workup

  1. concentrationThen it was concentrated
  2. customthe oxalyl chloride carefully removed by distillation

Sources & evidence

ORD record
ord-1c89bec5474a4f3ca3430d937825a138
Source dataset
uspto-grants-2006_03
Patent number
US07019002B2

Reaction notes

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