Hydrochloric Acid → HCID 71078033, compound

HRID 1774481Notes

Reaction equation

HRID 1774481 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([NH:9]N)[CH:6]=[CH:7][CH:8]=1.[Br:11][C:12]1[CH:13]=[C:14]([S:18][CH2:19][C:20](=O)[CH3:21])[CH:15]=[N:16][CH:17]=1.Cl.CCOCC>C(O)(C)(C)C.C(O)(=O)C>[Br:11][C:12]1[CH:13]=[C:14]([S:18][C:19]2[C:6]3[C:5](=[CH:4][C:3]([Cl:2])=[CH:8][CH:7]=3)[NH:9][C:20]=2[CH3:21])[CH:15]=[N:16][CH:17]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 75331m-Chlorophenylhydrazine hydrochlorideHCID 71076691HCID 71076691, compound

Product 1

HCID 71078033HCID 71078033, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6386tert-ButanolSolvent

Conditions

Temperature
80 °C

Procedure

(3-Chloro-phenyl)-hydrazine hydrochloride (0.828 g, 4.63 mmol) and 1-(5-bromo-pyridin-3-ylsulfanyl)-propan-2-one (1.1 g, 4.63 mmol) were dissolved in tert-butanol (50 mL) and heated to 80° C. After heating overnight the reaction was cooled and concentrated. Purification on silica gel (0-50% EtOAc in hexanes) revealed the existence of hydrazone intermediates. The material was therefore resubmitted to the reaction conditions, with the addition of HCl in ether (13.9 mmol). After 2 hours acetic acid (2 mL) was added and the reaction continued to stir at 80° C. After stirring for 1 hour the reaction was cooled, concentrated and submitted to silica gel chromatography (10% MeOH in CH2Cl2) to afford a separable mixture of isomers, of which the first to elute from the column was the title compound.

Workup

  1. temperatureAfter heating overnight the reaction
  2. temperaturewas cooled
  3. concentrationconcentrated
  4. customPurification on silica gel (0-50% EtOAc in hexanes)
  5. stirringAfter stirring for 1 hour the reaction
  6. temperaturewas cooled
  7. concentrationconcentrated
  8. customto afford
  9. additiona separable mixture of isomers
  10. washof which the first to elute from the column

Sources & evidence

ORD record
ord-bf7471e1756e43289c6d7df3c0094a7e
Source dataset
uspto-grants-2016_02
Patent number
US09260416B2

Reaction notes

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