Chloroform → HCID 13376240, compound

HRID 280567Notes

Reaction equation

HRID 280567 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([O:10][CH2:11][CH2:12][N:13]2[CH:17]=[CH:16][N:15]=[CH:14]2)=[CH:8][CH:9]=1)=[O:4].C(Cl)(Cl)[Cl:19]>>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([O:10][CH2:11][CH2:12][N:13]2[CH:17]=[CH:16][N:15]=[CH:14]2)=[C:8]([Cl:19])[CH:9]=1)=[O:4]

Participants

3

Reactant 2

HCID 6212ChloroformHCID 13376215HCID 13376215, compound

Product 1

HCID 13376240HCID 13376240, compound

Conditions

Temperature
-40 °C

Procedure

0,15 g of 5-[2-(1-imidazolyl)-1-ethoxy]-thiophene-2-carboxylic-acid methyl ester (formula I: R=H, R1 =CH3) were dissolved in 5 ml of absolute chloroform, cooled to -40° C. and 0,16 g (1,19 mol) of SO2Cl2 were dropped thereto such that the temperature did not exceed -35° C. After standing over night it was evaporated in vacuo, the residue was partioned between 2N HCl and ether, the aqueous phase was extracted several times with ether, neutralized with sodium hydrogen carbonate and extracted several times with methylene chloride. The combined methylene chloride phases were dried (sodium sulfate) and evaporated, the residue from the evaporation was separated by column chromatography (eluant: benzene/ethanol 9:1). Yield 73 mg (43%), melting point 97°-99° C. (benzene/ether), colorless crystals.

Workup

  1. customdid not exceed -35° C
  2. waitAfter standing over night
  3. customit was evaporated in vacuo
  4. extractionthe aqueous phase was extracted several times with ether
  5. extractionextracted several times with methylene chloride
  6. dry with materialThe combined methylene chloride phases were dried (sodium sulfate)
  7. customevaporated
  8. customthe residue from the evaporation
  9. customwas separated by column chromatography (eluant: benzene/ethanol 9:1)

Sources & evidence

ORD record
ord-f8d7ade339b14c8c8292c634744402e0
Source dataset
uspto-grants-1986_05
Patent number
US04590203

Reaction notes

Loading…