Diazomethane → HCID 21445133, compound

HRID 597445Notes

Reaction equation

HRID 597445 reaction equation
[Cl:1][CH:2]([C:12]([CH3:14])=[O:13])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:4].[N+](=[CH2:17])=[N-]>C(Cl)Cl>[Cl:1]/[C:2](=[C:12](/[O:13][CH3:17])\[CH3:14])/[C:3]([NH:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)=[O:4]

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 1602123-Oxy-2-chlorobutanoic acid anylide

Product 1

HCID 21445133HCID 21445133, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

52.9 g of α-chloroacetoacetanilide in 500 ml of methylene chloride was held at 0° C for 4 hours and then 725 ml of methylene chloride solution titrating 17.4 g/l of diazomethane were added. The mixture was stirred for 16 hours at 0° C and then 1 hour at 20° C and was concentrated to dryness under reduced pressure. The residue was added to isopropyl ether and the precipitate formed was recovered by vacuum filtration and was crystallized from isopropyl ether to obtain 12 g of 2-chloro-3-methoxy-crotonanilide melting at 100° C.

Workup

  1. additionwere added
  2. concentration1 hour at 20° C and was concentrated to dryness under reduced pressure
  3. additionThe residue was added to isopropyl ether
  4. customthe precipitate formed
  5. filtrationwas recovered by vacuum filtration
  6. customwas crystallized from isopropyl ether

Sources & evidence

ORD record
ord-0db10d605ca949869791aec23a97e6b9
Source dataset
uspto-grants-1977_03
Patent number
US04014679

Reaction notes

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