m-Chloroperbenzoic acid → 3-Hydroxymethyl-10,11-dihydrodibenzo[b,f]thiepin-5-oxide

HRID 1732352Notes

Reaction equation

HRID 1732352 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:12][CH2:11][C:10]3[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=3[S:8][C:7]=2[CH:17]=1.ClC1C=CC=C(C(OO)=[O:26])C=1.[OH-].[Ca+2].[OH-]>C(Cl)Cl>[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:12][CH2:11][C:10]3[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=3[S:8](=[O:26])[C:7]=2[CH:17]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 6093208Calcium HydroxideHCID 202555023-Hydroxymethyl-10,11-dihydrodibenzo[b,f]thiepin

Product 1

HCID 202555043-Hydroxymethyl-10,11-dihydrodibenzo[b,f]thiepin-5-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Dissolve 2 gm. of 3-hydroxymethyl-10,11-dihydrodibenzo[b,f]thiepin in 200 ml. of methylene chloride at room temperature. Add 1.7 gm. of m-chloroperbenzoic acid. Stir at room temperature for 2 hours. Add 4 gm. of calcium hydroxide and 50 ml. of methylene chloride. Continue stirring for 15 minutes. Filter through celite and evaporate the filtrate to dryness. Crystallize the residue from toluene to obtain the title product (m.p., 144°-146° C.).

Workup

  1. dissolutionDissolve 2 gm
  2. customat room temperature
  3. additionAdd 1.7 gm
  4. additionAdd 4 gm
  5. stirringContinue stirring for 15 minutes
  6. filtrationFilter through celite
  7. customevaporate the filtrate to dryness
  8. customCrystallize the residue from toluene

Sources & evidence

ORD record
ord-a2fcbbd47c5647fcaf3aff6a31e97715
Source dataset
uspto-grants-1980_12
Patent number
US04237160

Reaction notes

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