Phenothiazine → 3-Methoxycyclohepta-1,3,5-triene

HRID 1413239Notes

Reaction equation

HRID 1413239 reaction equation
C1C2NC3C(=CC=CC=3)SC=2C=CC=1.[CH3:15][O:16][CH:17]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=[CH:18]1>>[CH3:15][O:16][C:17]1[CH:18]=[CH:19][CH2:20][CH:21]=[CH:22][CH:23]=1

Participants

3

Reactant 2

HCID 7108PhenothiazineHCID 1371707-Methoxycycloheptatriene

Product 1

HCID 125703443-Methoxycyclohepta-1,3,5-triene

Conditions

Temperature
150 °C

Procedure

Phenothiazine (1.4 gm=0.1% by weight of 7-methoxycycloheptatriene) was dissolved in 1381.9 gm of distilled 7-methoxycycloheptatriene. The solution was then heated under nitroen at ambient pressure for 2 hours at 150° C., during which time low-boiling materials were removed by a condenser set for downward distillation. Upon cooling, the residual material weighed 1345.2 grams, representing a crude yield of 97.3% (based on initial 7-methoxy isomer). NMR analysis indicated a product composition of 76 mole % 3-methoxycyclohepta-1,3,5-triene, 12 mole % 1-methoxycyclohepta-1,3,5-triene and 4 mole % unconverted 7-methoxy isomer. The product was of sufficiently good quality to be utilized for conversion to 1-methoxycycloheptatriene without prior distillation.

Workup

  1. customwere removed by a condenser
  2. distillationset for downward distillation
  3. temperatureUpon cooling
  4. distillationdistillation

Sources & evidence

ORD record
ord-9cf4a1201edd40fb857a1e8b544b2a1c
Source dataset
uspto-grants-1981_02
Patent number
US04249025

Reaction notes

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