Ethyl chloroformate → 131817-86-2

HRID 2371954Notes

Reaction equation

HRID 2371954 reaction equation
[CH3:1][C:2]1[N:3]([C:8]2[CH:13]=[CH:12][C:11](/[CH:14]=[CH:15]/[C:16]([OH:18])=O)=[CH:10][CH:9]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1.ClC(OCC)=O.Cl.[CH3:26][NH:27][OH:28]>ClCCl.C(N(CC)CC)C>[CH3:1][C:2]1[N:3]([C:8]2[CH:13]=[CH:12][C:11](/[CH:14]=[CH:15]/[C:16]([N:27]([OH:28])[CH3:26])=[O:18])=[CH:10][CH:9]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 10928Ethyl chloroformateHCID 77906N-methylhydroxylamine hydrochlorideHCID 19905460HCID 19905460, compound

Product 1

HCID 6439321131817-86-2

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent2×

Procedure

A solution of 12.05 g of (E)-3-[4-(2,5-dimethyl-1H-pyrrol-1-yl)-phenyl]-2-propenoic acid in 350 ml of dichloromethane and 9.7 ml triethylamine, is cooled in an ice bath. To this stirred solution is added 7.0 ml of ethyl chloroformate dropwise. After four hours at ice-bath temperature, 20.7 ml of triethylamine is added, followed by 12.6 g of N-methylhydroxylamine hydrochloride and the mixture is kept at room temperature for 16 hours. This mixture is washed with cold 0.3 N aqueous hydrochloric acid, ice cold sodium bicarbonate and brine. The organic phase is dried over MgSO4, treated with charcoal and filtered. The solvent is evaporated at 50° under reduced pressure and the product is crystallized from ether to give (E)-3-[4-(2,5-dimethyl-1H-pyrrol-1-yl)-phenyl]-N-hydroxy-N-methyl-2-propenamide, m.p. 143°-145°, the compound of formula IV wherein R1 and R2 represent methyl at the 2 and 5 positions, R4 represents methyl, and R3, R8 and R9 represent hydrogen; the compound may also be named (E)-3-[4-(2,5-dimethyl-1H-pyrrol-1-yl)-phenyl]-N-methyl-2-propenohydroxamic acid. The product can also be recrystallized from ethyl acetate (with charcoal and silica gel).

Workup

  1. washThis mixture is washed with cold 0.3 N aqueous hydrochloric acid, ice cold sodium bicarbonate and brine
  2. dry with materialThe organic phase is dried over MgSO4
  3. additiontreated with charcoal
  4. filtrationfiltered
  5. customThe solvent is evaporated at 50° under reduced pressure
  6. customthe product is crystallized from ether

Sources & evidence

ORD record
ord-c55c95ce7fd041f3b2ca5065fba372ee
Source dataset
uspto-grants-1992_03
Patent number
US05096919

Reaction notes

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