Hydrochloric Acid → HCID 13604761, compound

HRID 255907Notes

Reaction equation

HRID 255907 reaction equation
[N+]([C:4]([CH3:16])=[CH:5][C:6]1[S:7][CH:8]=[C:9]([N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)[CH:10]=1)([O-])=O.[OH2:17].Cl>[Fe].CO>[N:11]1([C:9]2[CH:10]=[C:6]([CH2:5][C:4](=[O:17])[CH3:16])[S:7][CH:8]=2)[CH:15]=[CH:14][N:13]=[CH:12]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 56616504HCID 56616504, compound

Product 1

HCID 13604761HCID 13604761, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent2×

Procedure

A mixture of 34 g (1-[2-(2-nitro-1-propenyl)-4-thienyl]-imidazole, 65 g iron powder, 0.9 ferrichloride hexahydrate, 51 ml methanol and 100 ml water are heated to reflux temperature while stirring. At this temperature, 65 ml concentrated hydrochloric acid are added dropwise within 1 hour. Subsequently, stirring is continued for 11/2 hours under reflux. After cooling, the mixture is stirred into 4 times the amount of methanol. Then, it is filtrated. The filtrate is evaporated to about 1/5 of its volume and filled up with water to 500 ml. The precipitated brown deposit is sucked off, then the filtrate is extracted several times with dichloromethane. The united dichloromethane phases are dried and evaporated. The residual crude product is used in the following reaction steps without further purification.

Workup

  1. temperatureare heated
  2. temperatureto reflux temperature
  3. stirringSubsequently, stirring
  4. custom2 hours
  5. temperatureunder reflux
  6. temperatureAfter cooling
  7. filtrationThen, it is filtrated
  8. customThe filtrate is evaporated to about 1/5 of its volume
  9. additionfilled up with water to 500 ml
  10. extractionthe filtrate is extracted several times with dichloromethane
  11. dry with materialThe united dichloromethane phases are dried
  12. customevaporated
  13. customThe residual crude product is used in the following reaction steps without further purification

Sources & evidence

ORD record
ord-65d426a046084f90bce272b233cdfec1
Source dataset
uspto-grants-1987_10
Patent number
US04699914

Reaction notes

Loading…