Methanethiol → HCID 21162718, compound

HRID 894205Notes

Reaction equation

HRID 894205 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.CC(C)([O-])C.[K+].CS>O.CN(C)C=O>[CH:16]1[C:3]2[CH2:2][C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[CH2:6][O:5][C:4]=2[CH:13]=[CH:14][C:15]=1[C:17]([O:19][CH3:20])=[O:18]

Participants

7

Reactant 4

HCID 878MethanethiolHCID 24386Thionyl Chloride2×HCID 2769059Methyl 11-hydroxy-6,11-dihydrobenzo[c][1]benzoxepine-2-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 21162718HCID 21162718, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

Reflux 4.4 gm. of methyl 6,11-dihydro-11-hydroxydibenz[b,e]oxepin-2-carboxylate with 20 ml. of thionyl chloride for 10 minutes. Evaporate excess thionyl chloride and dissolve the residue in 30 ml. of dimethylformamide. Add the mixture to a solution of 3.84 gm. of potassium tert-butoxide in 75 ml. of dimethylformamide saturated with methanethiol. Stir at room temperature for 24 hours, dilute with water and extract with ether. Evaporate to dryness and chromatograph over silica gel, eluting with toluene. Evaporate to dryness to obtain the title product as an oil (yield 3.03 gm., 84%).

Workup

  1. temperatureReflux 4.4 gm
  2. additionAdd the mixture to a solution of 3.84 gm
  3. extractionextract with ether
  4. customEvaporate to dryness and chromatograph over silica gel
  5. washeluting with toluene
  6. customEvaporate to dryness

Sources & evidence

ORD record
ord-19a6dad313b3475a9d3366f36b77e2b3
Source dataset
uspto-grants-1981_08
Patent number
US04282365

Reaction notes

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