Hydrochloric Acid → HCID 21271596, compound

HRID 247344Notes

Reaction equation

HRID 247344 reaction equation
[CH3:1][N:2]([CH3:21])[CH2:3][CH2:4][CH:5]1[CH2:11][N:10]([CH3:12])[C:9](=[S:13])[C:8]2[CH:14]=[C:15]([N+:18]([O-])=O)[CH:16]=[CH:17][C:7]=2[O:6]1.[NH4+]=S.C(O)C.Cl>O>[NH2:18][C:15]1[CH:16]=[CH:17][C:7]2[O:6][CH:5]([CH2:4][CH2:3][N:2]([CH3:1])[CH3:21])[CH2:11][N:10]([CH3:12])[C:9](=[S:13])[C:8]=2[CH:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 13726415HCID 13726415, compound

Product 1

HCID 21271596HCID 21271596, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 7.0 g (0.023 mole) of 2-[2-(dimethylamino)ethyl]-2,3-dihydro-4-methyl-7-nitro-1,4-benzoxazepine-5(4H)-thione was added 250 ml of 23% ammonium sulfide in water. Ethyl alcohol was added in amount sufficient to dissolve the starting compound (~50-60 ml). The reaction mixture was heated to reflux for 5 hr. After cooling, the reaction mixture was acidified with concentrated aqueous hydrochloric acid. The ethanol was removed by rotary evaporation at 70° C. The remaining aqueous solution was washed with 3×100 ml of chloroform, filtered, cooled with ice and made slightly basic with sodium hydroxide. The aqueous was then extracted with 3×100 ml of chloroform, dried over sodium sulfate, filtered and concentrated by rotary evaporation. The residue was crystallized from isopropyl alcohol to give 3.5 g (55%) of yellow analytically pure crystals.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 5 hr
  3. temperatureAfter cooling
  4. customThe ethanol was removed by rotary evaporation at 70° C
  5. washThe remaining aqueous solution was washed with 3×100 ml of chloroform
  6. filtrationfiltered
  7. temperaturecooled with ice
  8. extractionThe aqueous was then extracted with 3×100 ml of chloroform
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated by rotary evaporation
  12. customThe residue was crystallized from isopropyl alcohol
  13. customto give 3.5 g (55%) of yellow analytically pure crystals

Sources & evidence

ORD record
ord-b8188bc005cf43f996272e3cd4b46a5c
Source dataset
uspto-grants-1987_11
Patent number
US04705853

Reaction notes

Loading…