Oxalyl chloride → HCID 58415379, compound

HRID 2075256Notes

Reaction equation

HRID 2075256 reaction equation
[F:1][C:2]1[CH:10]=C(C=O)C=[CH:7][C:3]=1[C:4](O)=[O:5].C(Cl)(=O)[C:14](Cl)=[O:15].[CH2:19]([C:26]1[CH:31]=[CH:30][C:29]([NH2:32])=[C:28]([N+:33]([O-:35])=[O:34])[CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(N([CH:42]([CH3:44])[CH3:43])CC)(C)C.[OH2:45].[C:46]1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl.C1COCC1.CO.CCOC(C)=O.CN(C=O)C>[CH2:19]([C:26]1[CH:31]=[CH:30][C:29]([NH:32][C:4](=[O:5])[C:3]2[CH:7]=[CH:44][C:42]([CH:43]([O:15][CH3:14])[O:45][CH3:46])=[CH:10][C:2]=2[F:1])=[C:28]([N+:33]([O-:35])=[O:34])[CH:27]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

11

Reactant 5

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 521998p-Toluenesulfonic acid monohydrateHCID 13907841HCID 13907841, compoundHCID 184419582-Fluoro-4-formylbenzoic acid

Product 1

HCID 58415379HCID 58415379, compound

Reagents, catalysts & solvents 5

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Fluoro-4-formylbenzoic acid (0.300 g, 1.78 mmol) was slurried in 10 mL DCM and catalytic DMF was added, followed by oxalyl chloride (0.317 mL, 3.57 mmol). The reaction was allowed to stir several h. Upon consumption of the acid, the reaction was concentrated in vacuo and diluted with 7 mL THF. 4-Benzyl-2-nitrobenzenamine (0.611 g, 2.68 mmol) and diisopropylethylamine (0.622 mL, 3.57 mmol) was added as a solution in 5 mL THF. The reaction was allowed to stir overnight and worked up with EtOAc/saturated sodium bicarbonate, dried over sodium sulfate, filtered, and concentrated. The residue was treated with p-toluenesulfonic acid monohydrate (0.170 g, 0.892 mmol) and MeOH. After 1 h, the mixture was concentrated and adsorbed onto silica gel and purified by chromatography to give N-(4-benzyl-2-nitrophenyl)-4-(dimethoxymethyl)-2-fluorobenzamide. MS (ESI) m/z: Calculated: 424.1; Observed: 425.2 (M++1).

Workup

  1. customUpon consumption of the acid
  2. concentrationthe reaction was concentrated in vacuo
  3. additiondiluted with 7 mL THF
  4. stirringto stir overnight
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. concentrationthe mixture was concentrated
  9. custompurified by chromatography

Sources & evidence

ORD record
ord-fbe71d635bed4f85a214ec6ecec49502
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

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