Sulfuryl chloride → HCID 20380249, compound

HRID 1448587Notes

Reaction equation

HRID 1448587 reaction equation
[C:1]([NH:4][C:5]1[C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][S:8][CH:9]=1)(=[O:3])[CH3:2].S(Cl)([Cl:17])(=O)=O>C(Cl)(Cl)Cl>[C:1]([NH:4][C:5]1[C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][S:8][C:9]=1[Cl:17])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 821687HCID 821687, compound

Product 1

HCID 20380249HCID 20380249, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

40 g. of methyl 4-acetylamino-3-thiophene carboxylate are dissolved in 1 liter of absolute chloroform, and a solution of 27 g. of sulfuryl chloride in 100 ml. of absolute chloroform is then added dropwise within 20 minutes. The reaction solution is then boiled under reflux for 1 hour. The brownish colored solution obtained is cooled and when its temperature is 10°, 1 liter of ice water is added. The organic solution is then washed with 200 ml. of 5% sodium bicarbonate solution, dried over sodium sulfate, and evaporated to dryness in vacuo. The oily residue is triturated with 100 ml. of ether, whereupon crystallization takes place. The product is suction filtered and recrystallized from ethyl acetate, and methyl 4-acetylamino-5-chloro-3-thiophene carboxylate having a melting point of 119°-121° is obtained. The ethereal filtrate and the mother liquor from the ethyl acetate recrystallization are combined, evaporated to dryness, and the oil that remains is chromatographed on 300 g. of silica gel using methylene chloride/ethyl acetate (4:1) as eluent. An additional portion of methyl 4-acetylamino-5-chloro-3-thiophene carboxylate having a melting point of 119°-121° is obtained.

Workup

  1. temperatureunder reflux for 1 hour
  2. customThe brownish colored solution obtained
  3. temperatureis cooled
  4. customis 10°
  5. washThe organic solution is then washed with 200 ml
  6. dry with materialof 5% sodium bicarbonate solution, dried over sodium sulfate
  7. customevaporated to dryness in vacuo
  8. customThe oily residue is triturated with 100 ml
  9. customof ether, whereupon crystallization
  10. filtrationfiltered
  11. customrecrystallized from ethyl acetate, and methyl 4-acetylamino-5-chloro-3-thiophene carboxylate having a melting point of 119°-121°
  12. customis obtained
  13. customThe ethereal filtrate and the mother liquor from the ethyl acetate recrystallization
  14. customevaporated to dryness
  15. customthe oil that remains is chromatographed on 300 g

Sources & evidence

ORD record
ord-c8a48c1ad93a44e58375af29b1ef7b60
Source dataset
uspto-grants-1979_12
Patent number
US04180662

Reaction notes

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