Chloroform → HCID 20149580, compound

HRID 1982155Notes

Reaction equation

HRID 1982155 reaction equation
C(OC([NH:8][C:9](=[CH2:14])[C:10]([O:12][CH3:13])=[O:11])=O)CCC.[SH:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1.C(Cl)(Cl)[Cl:24]>CO>[ClH:24].[NH2:8][CH:9]([CH2:14][S:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)[C:10]([O:12][CH3:13])=[O:11]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 2401474-MercaptophenolHCID 54308324HCID 54308324, compound

Product 1

HCID 20149580HCID 20149580, compoundYield 80.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

20 g (100 mmol; 120 ml) methyl 2-(butoxycarbonylamino)-propenoate in chloroform was dissolved in 180 ml of methanol. 13.88 g (110 mmol) 4-mercaptophenol was added and the mixture was then stirred at room temperature under nitrogen for 24 hours. Solvents were removed in vacuo until foaming occurred, then the mixture was taken up in 700 ml dry ether. HCl gas was bubbled through the solution, quickly forming a white precipitate. Bubbling was continued for 1 hour with cooling, then the solution was cooled to 5° C. and filtered to yield the title compound in 80.8% yield.

Workup

  1. customSolvents were removed in vacuo
  2. customHCl gas was bubbled through the solution
  3. customquickly forming a white precipitate
  4. customBubbling
  5. waitwas continued for 1 hour
  6. temperaturewith cooling
  7. temperaturethe solution was cooled to 5° C.
  8. filtrationfiltered

Sources & evidence

ORD record
ord-59269a8f66b445309a0e1a37bde7624f
Source dataset
uspto-grants-1986_06
Patent number
US04595687

Reaction notes

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