Hydrochloric Acid → HCID 12750603, compound

HRID 234166Notes

Reaction equation

HRID 234166 reaction equation
[N+]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]1[CH:15]=[CH:14][S:13][C:12]=1[C:16]1[O:17]C=C[N:20]=1)([O-])=O.Cl>CC(C)=O.O>[S:13]1[C:12]2[C:16](=[O:17])[NH:20][C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[CH2:10][C:11]=2[CH:15]=[CH:14]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 23358477HCID 23358477, compound

Product 1

HCID 12750603HCID 12750603, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Conditions

Temperature
70 °C

Procedure

A mixture of 5.0 g of the product of Example 5 in 100 ml of 3:1 acetone-water containing 30 ml of 1N HCl is refluxed for 24 hours. The reaction mixture is concentrated in vacuo to a residue which is dissolved in 100 ml of glacial acetic acid. The mixture is stirred at 70° C. while 10.0 g of zinc dust is slowly added. Stirring is continued for 6 hours. The reaction mixture is cooled to room temperature and filtered. The filtrate is evaporated in vacuo to a residue which is extracted with chloroform. The organic layer is dried over sodium sulfate and concentrated in vacuo to give 2.9 g of the desired product as a brown solid, M+ =215.

Workup

  1. temperatureis refluxed for 24 hours
  2. concentrationThe reaction mixture is concentrated in vacuo to a residue which
  3. dissolutionis dissolved in 100 ml of glacial acetic acid
  4. additionis slowly added
  5. stirringStirring
  6. temperatureThe reaction mixture is cooled to room temperature
  7. filtrationfiltered
  8. customThe filtrate is evaporated in vacuo to a residue which
  9. extractionis extracted with chloroform
  10. dry with materialThe organic layer is dried over sodium sulfate
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bd905fe443fd46308cc46e4354e9b7e1
Source dataset
uspto-grants-1997_01
Patent number
US05594152

Reaction notes

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