Dimethylformamide → HCID 44478829, compound

HRID 340656Notes

Reaction equation

HRID 340656 reaction equation
C(=O)([O-])[O-].[K+].[K+].CN(C=O)C.Br.[OH:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[N:21]=[C:22]3[N:26]([CH:27]=2)[CH:25]=[CH:24][S:23]3)=[CH:16][C:15]=1[O:28][CH3:29].[Cl:30][C:31]1[CH:38]=[CH:37][C:34]([CH2:35]Br)=[CH:33][CH:32]=1>O.CO>[Cl:30][C:31]1[CH:38]=[CH:37][C:34]([CH2:35][O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[N:21]=[C:22]4[N:26]([CH:27]=3)[CH:25]=[CH:24][S:23]4)=[CH:16][C:15]=2[O:28][CH3:29])=[CH:33][CH:32]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 69813198HCID 69813198, compound

Product 1

HCID 44478829HCID 44478829, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Potassium carbonate (106 g) was added to 490 ml of an anhydrous DMF suspension of 120 g of the compound obtained in Step 1. After stirring for 2 hours, to the mixture was added 82.9 g of p-chlorobenzyl bromide at 0° C., and stirred for 3 hours at 0° C. and for 42 hours at room temperature. The reaction mixture was mixed with 500 ml of methanol and 450 ml of water, and stirred at 70° C. for 30 minutes. After cooling the mixture to room temperature, the precipitated crystals were suction filtered, rinsed with 50% methanol and water, and dried under reduced pressure, thereby yielding 102 g of transparent crystals of the desired compound (“Example Compound 23”).

Workup

  1. stirringstirred for 3 hours at 0° C. and for 42 hours at room temperature
  2. stirringstirred at 70° C. for 30 minutes
  3. filtrationfiltered
  4. washrinsed with 50% methanol and water
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-d4c7b5404fb547aa84cfccbaf3d1a884
Source dataset
uspto-grants-2014_11
Patent number
US08895599B2

Reaction notes

Loading…