Dimethylformamide → HCID 18994620, compound

HRID 375245Notes

Reaction equation

HRID 375245 reaction equation
CN(C)C=O.[C:6]1([N:12]2[C:21]3[N:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:15]3[N:22]=[CH:23][NH:24][C:14]=3[C:13]2=[S:25])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[H-].[Na+].[CH2:28](Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>O>[CH2:28]([S:25][C:13]1[N:12]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:21]2[N:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:15]2[C:14]=1[N:24]=[CH:23][N:22]=2)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 9903756HCID 9903756, compound

Product 1

HCID 18994620HCID 18994620, compoundYield 43.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into 30 ml of dimethylformamide was dissolved 0.79 g (2.5 mmol) of Compound 1 obtained in Example 1. Furthermore, 0.13 g (3.4 mmol) of 60% sodium hydride was added thereto with stirring at room temperature. The mixture was stirred for 1 hour. Then, 0.41 ml (3.4 mmol) of benzyl bromide was added thereto, followed by further stirring for 1 hour. The mixture was cooled with ice and then water was added thereto. The precipitated solid was collected by filtration. The solid was dried, dissolved into chloroform and purified by silica gel column chromatography (eluent: chloroform) to give 0.25 g (24%) of Compound (II) as the first fractions and 0.40 g (38%) of Compound 3 as the second fractions.

Workup

  1. stirringThe mixture was stirred for 1 hour
  2. stirringby further stirring for 1 hour
  3. temperatureThe mixture was cooled with ice
  4. filtrationThe precipitated solid was collected by filtration
  5. customThe solid was dried
  6. dissolutiondissolved into chloroform
  7. custompurified by silica gel column chromatography (eluent: chloroform)

Sources & evidence

ORD record
ord-1f429f7712564edcb18bd08fc4bd7561
Source dataset
uspto-grants-1996_01
Patent number
US05484924

Reaction notes

Loading…