Hydrochloric Acid → 1,5-Benzothiazepin-4(5H)-one, 2,3-dihydro-

HRID 1709297Notes

Reaction equation

HRID 1709297 reaction equation
[OH-:1].[Na+].[S:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[CH:4]1.Cl.ClC1C=CC=C[C:15]=1[CH3:20].ClC1C=CC(C)=CC=1>O>[S:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[NH:5][C:4](=[O:1])[CH2:20][CH2:15]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7222BenzothiazoleHCID 72382-Chlorotoluene2×HCID 78104-ChlorotolueneHCID 14798Sodium Hydroxide

Product 1

HCID 964711,5-Benzothiazepin-4(5H)-one, 2,3-dihydro-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

100 parts by weight of 50% NaOH solution were initially introduced and heated to reflux. 66 parts by weight of benzothiazole were added in the course of 3 hours and the mixture was then stirred under reflux for 2 h. It was then cooled somewhat and acidified at 100° C. with 120 parts by weight of conc. HCl and a further 100 parts by weight of water were then added. 70 parts by weight of a chlorotoluene mixture comprising about 50% o-chlorotoluene and about 50% p-chlorotoluene were added and the separating water phase was separated off. The organic phase was heated to 100° C., 35 parts by weight of acrylic acid were added in the course of 1 hour and the mixture was heated to reflux until water no longer separated from the condensate. The organic phase of the condensate was fed back into the reaction mixture. The mixture was then cooled to about 25° C. and the solid was filtered off with suction. It was washed with 70 parts by weight of the chlorotoluene mixture.

Workup

  1. temperatureheated to reflux
  2. temperatureunder reflux for 2 h
  3. temperatureIt was then cooled somewhat
  4. customthe separating water phase was separated off
  5. addition35 parts by weight of acrylic acid were added in the course of 1 hour
  6. temperaturethe mixture was heated
  7. temperatureto reflux until water
  8. customno longer separated from the condensate
  9. temperatureThe mixture was then cooled to about 25° C.
  10. filtrationthe solid was filtered off with suction
  11. washIt was washed with 70 parts by weight of the chlorotoluene mixture

Sources & evidence

ORD record
ord-e5e2a2512b7b463ebbf18b5ede42a9f2
Source dataset
uspto-grants-1990_08
Patent number
US04948886

Reaction notes

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