Sodium hydride → HCID 67596032, compound

HRID 442859Notes

Reaction equation

HRID 442859 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[NH:17][C:18]3[C:23]([C:24]=2[CH:25]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:15])[CH2:10][CH2:9]1.[H-].[Na+].Cl.[CH3:41][N:42]([CH3:46])[CH2:43][CH2:44]Cl.[Cl-].[NH4+]>CN(C)C=O.O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[N:17]([CH2:44][CH2:43][N:42]([CH3:46])[CH3:41])[C:18]3[C:23]([C:24]=2[CH:25]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:15])[CH2:10][CH2:9]1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 15858911HCID 15858911, compound

Product 1

HCID 67596032HCID 67596032, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of Compound 88 (1.0 g, 1.98 mmol) obtained in Example 88 in 10 ml of N,N-dimethylformamide was portionwise added sodium hydride (60% in oil, 166 mg, 4.15 mmol) with stirring at room temperature, and 2-dimethylaminoethylchloride hydrochloride (298 mg, 2.07 mmol) was added thereto, followed by heating to 80° C. and then stirring for one hour. A saturated aqueous solution of ammonium chloride was added to the reaction solution for neutralization, water was added thereto, and the resulting crystals were collected by filtration to give 1.1 g of a crude product. The obtained crude product was recrystallized from ethanol (65 ml) to give 0.67 g (yield: 59%) of the title compound.

Workup

  1. temperatureby heating to 80° C.
  2. stirringstirring for one hour
  3. additionwas added
  4. filtrationthe resulting crystals were collected by filtration
  5. customto give 1.1 g of a crude product
  6. customThe obtained crude product
  7. customwas recrystallized from ethanol (65 ml)

Sources & evidence

ORD record
ord-978bb373ba5f480ab38ea80f15044d1d
Source dataset
uspto-grants-1999_04
Patent number
US05891902

Reaction notes

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