Dimethylcarbamoyl Chloride → HCID 9861062, compound

HRID 612455Notes

Reaction equation

HRID 612455 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([NH:7][N:8]2[CH2:16][C:15]3[C:14]([OH:17])=[CH:13][CH:12]=[CH:11][C:10]=3[CH2:9]2)=[CH:3][CH:2]=1.C(N(CC)CC)C.[CH3:25][N:26]([CH3:30])[C:27](Cl)=[O:28].C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[CH3:25][N:26]([CH3:30])[C:27](=[O:28])[O:17][C:14]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:15]=1[CH2:16][N:8]([NH:7][C:4]1[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=1)[CH2:9]2

Participants

6

Reactant 4

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 9859383HCID 9859383, compound

Product 1

HCID 9861062HCID 9861062, compoundYield 60.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixture of 2,3-dihydro-2-(4-pyridinylamino)-1H-isoindol-4-ol (1.20 g), triethylamine (1.18 g) and chloroform (35 ml), was added dimethylcarbamyl chloride (0.68 g) with stirring, at ambient temperature, under nitrogen. The reaction mixture was heated under reflux for 3 hrs, poured into dilute sodium bicarbonate solution (100 ml), and the layers were separated. The aqueous phase was extracted with chloroform, and the combined organic extracts were dried over anhydrous sodium sulfate, filtered, and the filtrate was evaporated. The residue was chromatographed on silica, eluting with 10-15% methanol/dichloromethane. The appropriate fractions were collected and concentrated to give 953 mg (60%) of product. Recrystallization from dichloromethane-heptane gave the analytical sample, mp 183-185° C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 3 hrs
  3. customthe layers were separated
  4. extractionThe aqueous phase was extracted with chloroform
  5. dry with materialthe combined organic extracts were dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customthe filtrate was evaporated
  8. customThe residue was chromatographed on silica
  9. washeluting with 10-15% methanol/dichloromethane
  10. customThe appropriate fractions were collected
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-77a5c7087d17420385a45e164c14e093
Source dataset
uspto-grants-1999_12
Patent number
US06004977

Reaction notes

Loading…