Dimethylformamide → HCID 86696920, compound

HRID 880047Notes

Reaction equation

HRID 880047 reaction equation
[C:1]1([N:7]2[C:12](=[O:13])[NH:11][C:10](=[O:14])[C:9]([C:15]#[N:16])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C=O)C.[H-].[Na+].[CH2:24](Br)[CH2:25][CH2:26][CH3:27]>O>[C:1]1([N:7]2[C:12](=[O:13])[N:11]([CH2:24][CH2:25][CH2:26][CH3:27])[C:10](=[O:14])[C:9]([C:15]#[N:16])=[N:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8002Butyl bromideHCID 24758Sodium hydrideHCID 563387HCID 563387, compound

Product 1

HCID 86696920HCID 86696920, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Intermediate c (9 g, 0.042 mol) was added to DMF (100 mL). To the mixture was added NaH (1.3 g, 0.054 mol) in batch under an ice bath. After stirring for 30 min, n-butyl bromide (3.4 mL, 0.042 mol) was added dropwise. Ater the dropwise addition, the reaction was conducted at 70° C. for 6 h. After completion of the reaction, the reaction solution was poured into water (600 mL). A great deal of solid separated out and was filtered by suction. The filtered cake was washed with water and dried to produce Intermediate f (8.2 g) in a yield of 81.4%.

Workup

  1. additionAter the dropwise addition
  2. waitthe reaction was conducted at 70° C. for 6 h
  3. customAfter completion of the reaction
  4. customA great deal of solid separated out
  5. filtrationwas filtered by suction
  6. washThe filtered cake was washed with water
  7. customdried

Sources & evidence

ORD record
ord-028462de4cb6418981cbde3d311a603f
Source dataset
uspto-grants-2015_03
Patent number
US08993566B2

Reaction notes

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