Hydrochloric Acid → HCID 21467138, compound

HRID 1733939Notes

Reaction equation

HRID 1733939 reaction equation
[N+:1]([C:4]1[CH:22]=[CH:21][C:7]([C:8]([N:10]2[CH2:16][CH2:15][CH2:14][C:13](=[O:17])[C:12]3[S:18][CH:19]=[CH:20][C:11]2=3)=[O:9])=[CH:6][CH:5]=1)([O-])=O.Cl>C(O)(=O)C.[Fe]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:8]([N:10]2[CH2:16][CH2:15][CH2:14][C:13](=[O:17])[C:12]3[S:18][CH:19]=[CH:20][C:11]2=3)=[O:9])=[CH:21][CH:22]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 196990654,5,6,7-tetrahydro-4-(4-nitrobenzoyl)-8H-thieno[3,2-b]azepin-8-one

Product 1

HCID 21467138HCID 21467138, compoundYield 68.5%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

To a mixture of 2.0 g of 4-(4-nitrobenzoyl)-4,5,6,7-tetrahydro-8H-thieno[3,2-b]azepin-8-one in 40 ml of glacial acetic acid is added 20 ml of 6N-hydrochloric acid. The mixture is cooled and 3.53 g of iron powder added in portions. The mixture is allowed to warm to room temperature and is heated at 70°-80° C. for 1 hour and then cooled to 0° C. To mixture is basified with 10N NaOH(pH 14) and extracted with 200 ml of ethyl acetate. The aqueous layer is again extracted with 200 ml of ethyl acetate and the extracts combined. The combined extract is washed with 100 ml each of H2O and brine and dried (Na2SO4). The extract is filtered through a thin pad of hydrous magnesium silicate and the filtrate concentrated to give a solid which is crystallized from ethyl acetate-hexane to give 1.24 g of crystals, m.p. 216°-218° C.

Workup

  1. temperatureThe mixture is cooled
  2. temperatureis heated at 70°-80° C. for 1 hour
  3. temperaturecooled to 0° C
  4. extractionextracted with 200 ml of ethyl acetate
  5. extractionThe aqueous layer is again extracted with 200 ml of ethyl acetate
  6. extractionThe combined extract
  7. washis washed with 100 ml each of H2O and brine
  8. dry with materialdried (Na2SO4)
  9. filtrationThe extract is filtered through a thin pad of hydrous magnesium silicate
  10. concentrationthe filtrate concentrated
  11. customto give a solid which
  12. customis crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-6e3c021a570b4761974e27f0e7997921
Source dataset
uspto-grants-1996_07
Patent number
US05532235

Reaction notes

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