Dimethylformamide → HCID 46856259, compound

HRID 717338Notes

Reaction equation

HRID 717338 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][CH:14]=1.[Cl:22]CCl.C(Cl)(=O)C(Cl)=O.CN(C)C=O>C(OCC)(=O)C>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([Cl:22])=[O:18])=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 7475534-[(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)methyl]benzoic acid

Product 1

HCID 46856259HCID 46856259, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

Into a 500-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 4-[(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)methyl]benzoic acid (15.7 g, 55.82 mmol, 1.00 equiv), dichloromethane (200 mL), oxalic dichloride (10.56 g, 83.20 mmol, 1.49 equiv) and dimethylforamide (cat.). The resulting solution was stirred for 2 h at 25° C. The resulting mixture was concentrated under vacuum. This resulted in 16.7 g (crude) of 4-[(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)methyl]benzoyl chloride as a white solid. Rf: 0.30 (in ethyl acetate:petroleum ether=1:5).

Workup

  1. customInto a 500-mL 3-necked round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. concentrationThe resulting mixture was concentrated under vacuum
  4. customThis resulted in 16.7 g (crude) of 4-[(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)methyl]benzoyl chloride as a white solid

Sources & evidence

ORD record
ord-083f1c78b6164b95be305bd9336ef47b
Source dataset
uspto-grants-2015_11
Patent number
US09193707B2

Reaction notes

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