Dimethylformamide → HCID 86679345, compound

HRID 1498920Notes

Reaction equation

HRID 1498920 reaction equation
[CH3:1]N(C)C=O.CI.C(=O)([O-])[O-].[K+].[K+].CO[C:16]1[CH:34]=[CH:33][C:19]([CH2:20][NH:21][N:22]2[C:30](=[O:31])[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:23]2=[O:32])=C[C:17]=1C.[C:36]([O:39][CH2:40][CH3:41])(=O)C.C1(C)C=CC=CC=1>>[CH3:36][O:39][C:40]1[CH:41]=[CH:1][C:33]([CH2:19][CH2:20][NH:21][N:22]2[C:23](=[O:32])[C:24]3[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:30]2=[O:31])=[CH:34][C:16]=1[CH3:17]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 6328Methyl iodide2×HCID 11430Potassium CarbonateHCID 21584019Toluene ethylacetateHCID 68017766HCID 68017766, compound

Product 1

HCID 86679345HCID 86679345, compoundYield 65%

Procedure

N,N-dimethylformamide (20 ml), methyl iodide (0.7 ml) and potassium carbonate (3.12 g) were added to 2-(4-methoxy-3-methylbenzylamino)isoindole-1,3-dione (1.67 g) prepared in the Step 15-1-2, and the mixture was stirred overnight. Methyl iodide (0.35 ml) was added thereto, and the resulting mixture was stirred for another 5 hours. Thereafter, an ethyl acetate-toluene (3:1) solution was added thereto. The resulting mixture was washed with water and a saturated saline solution in order, and then dried over sodium sulfate and concentrated under a reduced pressure. To the resulting residue, diethyl ether was added, and the mixture was stirred at a room temperature. The precipitate was separated by filtration, washed with diethyl ether, and dried under a reduced pressure to give the title compound (1.15 g, 65%).

Workup

  1. customprepared in the Step 15-1-2
  2. stirringthe resulting mixture was stirred for another 5 hours
  3. washThe resulting mixture was washed with water
  4. dry with materiala saturated saline solution in order, and then dried over sodium sulfate
  5. concentrationconcentrated under a reduced pressure
  6. additionTo the resulting residue, diethyl ether was added
  7. stirringthe mixture was stirred at a room temperature
  8. customThe precipitate was separated by filtration
  9. washwashed with diethyl ether
  10. customdried under a reduced pressure

Sources & evidence

ORD record
ord-33150ecfdd1a416da5b839fb493dc9f8
Source dataset
uspto-grants-2015_12
Patent number
US09200008B2

Reaction notes

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