Dimethylformamide → HCID 59651994, compound

HRID 2042538Notes

Reaction equation

HRID 2042538 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]3[S:14][CH:15]=[CH:16][C:12]=3[C:11](=[O:17])[N:10]([CH:18]([CH3:20])[CH3:19])[N:9]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:28][CH2:29][CH2:30][Cl:31].CN(C=O)C>CC(C)=O>[Cl:31][CH2:30][CH2:29][CH2:28][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:13]3[S:14][CH:15]=[CH:16][C:12]=3[C:11](=[O:17])[N:10]([CH:18]([CH3:20])[CH3:19])[N:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 135982272HCID 135982272, compound

Product 1

HCID 59651994HCID 59651994, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of the product of step 3 (858 mg, 3 mmol), K2CO3 (1.24 g, 3.0 eq.), and 3-bromo-1-chloropropane (0.3 mL, 1.05 eq.) in acetone:DMF (25 mL:3 mL) was heated to 80° C. overnight. The mixture was then filtered, washed with acetone, and concentrated to dryness to afford the product of step 4 (1.17 mg, 98% yield): Mp 92-4° C.; MS m/z 363 (M+H).

Workup

  1. filtrationThe mixture was then filtered
  2. washwashed with acetone
  3. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-3620cec29ad4421eaa11557e76b99dbe
Source dataset
uspto-grants-2013_11
Patent number
US08586588B2

Reaction notes

Loading…