Dichloromethane → HCID 59488844, compound

HRID 1960164Notes

Reaction equation

HRID 1960164 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[O:7])=[CH:4][C:3]=1[N+:18]([O-:20])=[O:19].[H-].[Na+].Cl[CH2:24][O:25][CH2:26][CH3:27].ClCCl>CO>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([NH:8][C:9]2[CH:10]=[CH:11][C:12]([O:15][CH2:24][O:25][CH2:26][CH3:27])=[CH:13][CH:14]=2)=[O:7])=[CH:4][C:3]=1[N+:18]([O-:20])=[O:19]

Participants

6

Reactant 4

HCID 6344Dichloromethane2×HCID 18523Chloromethyl ethyl etherHCID 24758Sodium hydrideHCID 59488862HCID 59488862, compound

Product 1

HCID 59488844HCID 59488844, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

4-Chloro-N-(4-hydroxy-phenyl)-3-nitro-benzamide (14.6 g, 0.05 mol) was placed in an oven dried 2-necked 500 ml round-bottomed flask and flushed with N2. Enough Dimethoxyethane (DME, 100 ml) was added to dissolve the amide. The mixture was cooled in ice bath and sodium hydride (NaH, 50% in oil, 3.6 g total, 0.075 mol) added in small portions with vigorous stirring. An hour after addition was complete, chloromethoxy-ethane (7.13 g, 0.075 mol, commercially available) was added drop wise via a pressure-equalising dropping funnel. The reaction was followed by TLC (dichloromethane, DCM:methanol, MeOH, 95:5). The reaction mixture was poured into ice water and extracted with EtOAc (3×50 ml). The organic phase was dried (MgSO4) and evaporated under reduced pressure. The crude product was recrystallised form Hexane/ethyl acetate, 1:4. to give 81% of the title compound.

Workup

  1. customdried 2-necked 500 ml round-bottomed flask
  2. customflushed with N2
  3. additionEnough Dimethoxyethane (DME, 100 ml) was added
  4. dissolutionto dissolve the amide
  5. temperatureThe mixture was cooled in ice bath
  6. additionAn hour after addition
  7. extractionextracted with EtOAc (3×50 ml)
  8. dry with materialThe organic phase was dried (MgSO4)
  9. customevaporated under reduced pressure
  10. customThe crude product was recrystallised form Hexane/ethyl acetate, 1:4

Sources & evidence

ORD record
ord-dab9dd16064b4cfbb4cd686c897abded
Source dataset
uspto-grants-2013_04
Patent number
US08410312B2

Reaction notes

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