Dimethylformamide → HCID 21162713, compound

HRID 894202Notes

Reaction equation

HRID 894202 reaction equation
O[CH:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][O:5][C:4]2[CH:13]=[CH:14][C:15]([C:17]([O:19][CH3:20])=[O:18])=[CH:16][C:3]1=2.S(Cl)(Cl)=O.CN(C)C=O.[Na+].[CH3:31][S:32]([O-:34])=[O:33]>O>[CH3:31][S:32]([CH:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][O:5][C:4]2[CH:13]=[CH:14][C:15]([C:17]([O:19][CH3:20])=[O:18])=[CH:16][C:3]1=2)(=[O:34])=[O:33]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 2733271Sodium methanesulfinateHCID 2769059Methyl 11-hydroxy-6,11-dihydrobenzo[c][1]benzoxepine-2-carboxylate

Product 1

HCID 21162713HCID 21162713, compoundYield 68.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Reflux 1.4 gm. of methyl 6,11-dihydro-11-hydroxydibenz[b,e]oxepin-2-carboxylate in 6 cc. of thionyl chloride for 10 minutes. Strip away excess thionyl chloride by evaporation and dissolve the chloro intermediate so produced in 14 cc. of N,N-dimethylformamide. Add 582 mg. of methanesulfinic acid sodium salt (10% excess). Stir at room temperature for 5 days. Dilute with water and separate the solids by filtration. Crystallize from 15 cc. of benzene to obtain the title product (yield 1.18 gm. 68.6%).

Workup

  1. temperatureReflux 1.4 gm
  2. customStrip away excess thionyl chloride by evaporation
  3. dissolutiondissolve the chloro intermediate
  4. customso produced in 14 cc
  5. additionAdd 582 mg
  6. customseparate the solids
  7. filtrationby filtration
  8. customCrystallize from 15 cc

Sources & evidence

ORD record
ord-1c9ffca1b4cc4110bc7077c60b236f4f
Source dataset
uspto-grants-1981_08
Patent number
US04282365

Reaction notes

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