Ethanol → HCID 13827107, compound

HRID 978352Notes

Reaction equation

HRID 978352 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[C:5]1[C:10]([CH2:11][CH3:12])=[CH:9][C:8]([N+:13]([O-:15])=[O:14])=[CH:7][C:6]=1[NH2:16])[CH3:2].Cl[C:19]([O:21][C:22](Cl)(Cl)Cl)=[O:20].[CH2:26](O)C.C(N(CC)CC)C>C(OCC)(=O)C>[C:19]([NH:16][C:6]1[CH:7]=[C:8]([N+:13]([O-:15])=[O:14])[CH:9]=[C:10]([CH2:11][CH3:12])[C:5]=1[C:4]([O:3][CH2:1][CH3:2])=[O:17])([O:21][CH2:22][CH3:26])=[O:20]

Participants

6

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 10426DiphosgeneHCID 13827104HCID 13827104, compound

Product 1

HCID 13827107HCID 13827107, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of ethyl-2-amino-6-ethyl-4-nitro-benzoate (400 mg) in ethyl acetate (10 ml) was added dropwise to a solution of trichloromethyl chloroformate in ethylacetate (10 ml). A precipitate was formed immediately which dissolved on prolonged sitrring for 21/2 hours. A solution of ethanol (5 ml) and triethylamine (5 ml) was added. A yellowish precipitate was formed. After 1 hour the solution was partitioned between ethylacetate and water. The ethylacetate layer was washed with brine solution, dried over magnesium sulfate and evaporated to a reddish oil. The material was further purified by column chromatography on silica gel (10% EtOAc:pet.ether) to give a solid material,

Workup

  1. customA precipitate was formed immediately which
  2. dissolutiondissolved on prolonged sitrring for 21/2 hours
  3. customA yellowish precipitate was formed
  4. customAfter 1 hour the solution was partitioned between ethylacetate and water
  5. washThe ethylacetate layer was washed with brine solution
  6. dry with materialdried over magnesium sulfate
  7. customevaporated to a reddish oil
  8. customThe material was further purified by column chromatography on silica gel (10% EtOAc:pet.ether)
  9. customto give a solid material

Sources & evidence

ORD record
ord-e8750dd5b88041dda87ce5572e779514
Source dataset
uspto-grants-1987_05
Patent number
US04665070

Reaction notes

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