Dibenzo[b,e]thiepin-11(6H)-one → Dibenzo[b,e]thiepin-11(6H)-one, oxime

HRID 1287923Notes

Reaction equation

HRID 1287923 reaction equation
[CH:1]1[C:11]2[C:10](=O)[C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[CH2:7][S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.Cl.[NH2:18][OH:19]>N1C=CC=CC=1>[CH:1]1[C:11]2[C:10](=[N:18][OH:19])[C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[CH2:7][S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 73741Dibenzo[b,e]thiepin-11(6H)-oneHCID 443297Hydroxyamine hydrochloride2×

Product 1

HCID 73794634Dibenzo[b,e]thiepin-11(6H)-one, oxime

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

19.7 G. of dibenzo[b,e]thiepin-11(6H)-one and 14.6 g. of hydroxylamine hydrochloride in 350 ml. of pyridine are stirred under reflux conditions for 16 hours. After the addition of a further 7.3 g. of hydroxylamine hydrochloride, the mixture is stirred for a further 5 hours under reflux conditions. The mixture is evaporated and purified by chromatography over aluminum oxide using chloroform and chloroform/methanol (93:3) for the elution. The purified product is recrystallized from acetone. There is obtained dibenzo[b,e]thiepin-11(6H)-one-oxime of melting point 241°-243° C.

Workup

  1. additionAfter the addition of a further 7.3 g
  2. customThe mixture is evaporated
  3. custompurified by chromatography over aluminum oxide
  4. washfor the elution
  5. customThe purified product is recrystallized from acetone

Sources & evidence

ORD record
ord-0b71075db16e47b086aeb1165e17c4f9
Source dataset
uspto-grants-1976_10
Patent number
US03985895

Reaction notes

Loading…