Hydrochloric Acid → 270917-08-3

HRID 1824711Notes

Reaction equation

HRID 1824711 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH3:12])[C:5]2[O:9][C:8](S)=[N:7][C:6]=2[CH:11]=1.[NH:13]1[CH2:19][CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.C(OCC)(=O)C.Cl>C1(C)C=CC=CC=1.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH3:12])[C:5]2[O:9][C:8]([N:13]3[CH2:19][CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)=[N:7][C:6]=2[CH:11]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 68163Hexahydro-1,4-diazepineHCID 178426087HCID 178426087, compound

Product 1

HCID 9903419270917-08-3

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Under nitrogen atmosphere, a suspension of 5-chloro-2-mercapto-7-methylbenzoxazole (70 g, 35 mol) in toluene (1.4 L) was added with homopiperazine (70 g, 0.35 mol) with stirring, and then the mixture was heated under reflux for 3 hours. The reaction mixture was cooled to room temperature, and poured into a mixture of ethyl acetate (0.7 L) and water (0.7 L). The mixture was added dropwise with 6 N hydrochloric acid (55 mL) with stirring to adjust its pH to 7.5. The separated organic layer was washed with water (1.2 L). The remaining organic layer was added with water (1.2 L), and then added dropwise with 6 N hydrochloric acid with stirring to adjust its pH to 1–1.5. The separated aqueous layer was added with ethyl acetate (1.4 L), and then added with 5 N aqueous sodium hydroxide (180 mL) with stirring to adjust its pH to 8.0. The separated organic layer was washed with water (1.4 L), and dried anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to obtain the title compound as a crude product (59 g). A solution of the crude product in ethyl acetate (1.2 L) was added with activated carbon (1.5 g), and the mixture was stirred for 30 minutes at room temperature. Then, the activated carbon was removed by filtration, and the solvent was evaporated under reduced pressure. The resultant solid was added with acetonitrile (177 mL), and was dissolved by warming the mixture to 60 C.° with stirring. The resultant uniform solution was left stand for cooling to room temperature over 1 hour, and then further cooled to 5 C.° The deposited crystals were collected by filtration, and dried under reduced pressure at 40 C.° for 4 hours to obtain the title compound (34 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. stirringwith stirring
  4. washThe separated organic layer was washed with water (1.2 L)
  5. additionThe remaining organic layer was added with water (1.2 L)
  6. additionadded dropwise with 6 N hydrochloric acid
  7. stirringwith stirring
  8. additionThe separated aqueous layer was added with ethyl acetate (1.4 L)
  9. additionadded with 5 N aqueous sodium hydroxide (180 mL)
  10. stirringwith stirring
  11. washThe separated organic layer was washed with water (1.4 L), and dried anhydrous magnesium sulfate
  12. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-e8d04f7529c34b2597a6782d77e0c92b
Source dataset
uspto-grants-2006_05
Patent number
US07045516B1

Reaction notes

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