Dimethylformamide → HCID 20041224, compound

HRID 1906477Notes

Reaction equation

HRID 1906477 reaction equation
C[C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:6][CH:7]=1.[H-].[Na+].Br[CH2:15][C:16]1[C:17]([CH2:22]Br)=[CH:18][CH:19]=[CH:20][CH:21]=1.[CH3:24]N(C)C=O>>[C:7]1([CH3:24])[CH:2]=[CH:3][CH:4]=[C:5]([S:8]([N:11]2[CH2:22][C:17]3[C:16](=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:15]2)(=[O:9])=[O:10])[CH:6]=1

Participants

5

Reactant 4

HCID 6228Dimethylformamide3×HCID 6269P-ToluenesulfonamideHCID 24758Sodium hydrideHCID 66665o-Bis(bromomethyl)benzene

Product 1

HCID 20041224HCID 20041224, compound

Procedure

A solution of 34.2 g (0.2 mol) of p-toluenesulfonamide in 100 ml of dry N,N-dimethylformamide was added dropwise to a suspension of 18.9 g (0.42 mol) of sodium hydride (50% oil dispersion) in 60 ml of N,N-dimethylformamide. The reaction was stirred at room temperature for one hour, followed by one hour at 60° C. A solution of 52.8 g (0.2 mol) of α,α'-dibromo-0-xylene in 300 ml of N,N-dimethylformamide was added at such a rate that the temperature of the reaction mixture remained between 60°-70° C. After further stirring for 48 hours at room temperature under nitrogen ice water was added to the reaction mixture. The precipitated solid was filtered and recrystallized from hot ethanol. Yield 33.58 g, m.p. 175°-177° C. NMR (CDCl3) δ 2.32 (3H, s), 4.5 (4H,s), 7.25 (8H, m).

Workup

  1. waitfollowed by one hour at 60° C
  2. customremained between 60°-70° C
  3. stirringAfter further stirring for 48 hours at room temperature under nitrogen ice water
  4. additionwas added to the reaction mixture
  5. filtrationThe precipitated solid was filtered
  6. customrecrystallized from hot ethanol

Sources & evidence

ORD record
ord-a8453ad1808c4e17800deba2eeb7299e
Source dataset
uspto-grants-1987_03
Patent number
US04652573

Reaction notes

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