Dichloromethane → HCID 178483171, compound

HRID 1410377Notes

Reaction equation

HRID 1410377 reaction equation
[C:1]([C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.C(Cl)Cl.C(N(CC)CC)C.[C:34]1([CH:40]([C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=2)[CH2:41][N:42]([CH3:60])[C:43](=[O:59])[CH:44]([NH:51][CH2:52][CH2:53][C:54]2[N:55]=[CH:56][NH:57][CH:58]=2)[C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>CN(C)C=O>[C:1]([C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([N:51]([CH:44]([C:43](=[O:59])[N:42]([CH2:41][CH:40]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:61]1[CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=1)[CH3:60])[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[CH2:52][CH2:53][C:54]1[N:55]=[CH:56][NH:57][CH:58]=1)=[O:13])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 6344DichloromethaneHCID 68132-Benzoylbenzoic AcidHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 178483172HCID 178483172, compound

Product 1

HCID 178483171HCID 178483171, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

2-Benzoylbenzoic acid (0.341 g, 1.51 mmol) was taken up in a 2M solution of oxalyl chloride in methylene chloride (1.5 mL, 3.0 mmol). One drop of N,N-dimethylformamide was added and the frothy mixture was stirred overnight and concentrated. A solution of the crude 2-benzoylbenzoyl chloride in methylene chloride (4 mL) followed by triethylamine (0.25 mL, 1.8 mmol) was added to the product of step 2 (0.220 g, 0.502 mmol). The mixture was heated at reflux for 2 hours and concentrated. The residue was taken up in 5:1 methanol/1 N aqueous lithium hydroxide (12 mL) and stirred for 1 hour. The reaction was again concentrated and the residue was partitioned between ethyl acetate and aqueous sodium bicarbonate solution. The organic layer was dried (sodium sulfate) and concentrated to afford a foamy amber solid. Flash chromatography over silica (methylene chloride/methanol) provided 0.229 g (71%) of product as a foamy pale amber solid: 1H NMR (CDCl3) δ 7.91-6.92 (m, 26H), 6.54-6.39 (m, 1H), 6.34-6.06 (m, 1H), 4.83-431 (m, 2H), 3.97-2.82 (m, 3H), 2.70-2.39 (m, 3H), 2.35-2.09 (m, 2H) ppm. MS (ESI) m/z 648 (M+H+).

Workup

  1. concentrationconcentrated
  2. temperatureThe mixture was heated
  3. temperatureat reflux for 2 hours
  4. concentrationconcentrated
  5. stirringstirred for 1 hour
  6. concentrationThe reaction was again concentrated
  7. customthe residue was partitioned between ethyl acetate and aqueous sodium bicarbonate solution
  8. dry with materialThe organic layer was dried (sodium sulfate)
  9. concentrationconcentrated
  10. customto afford a foamy amber solid

Sources & evidence

ORD record
ord-b528c316287c49ddba81975a724cd21e
Source dataset
uspto-grants-2014_12
Patent number
US08921547B2

Reaction notes

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