Ethanol → ethyl N-(3-methoxy-2-nitrophenyl)carbamate

HRID 2287538Notes

Reaction equation

HRID 2287538 reaction equation
[CH3:1][O:2][C:3]1[C:4]([N+:12]([O-:14])=[O:13])=[C:5]([CH:9]=[CH:10][CH:11]=1)C(O)=O.C([N:17]([CH2:20]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:29])C=CC=CC=1.[CH2:39]([OH:41])[CH3:40]>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[C:4]([N+:12]([O-:14])=[O:13])=[C:5]([NH:17][C:20](=[O:29])[O:41][CH2:39][CH3:40])[CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 786323-Methoxy-2-nitrobenzoic acidHCID 199401P,P-Diphenylphosphinic azide

Product 1

HCID 10537989ethyl N-(3-methoxy-2-nitrophenyl)carbamateYield 59.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A suspension of 3-methoxy-2-nitrobenzoic acid (10.0 g), triethylamine (5.13 g) and diphenylphosphoryl azide (14 g) in benzene (100 ml) was refluxed for 40 minutes, and ethanol (2.57 g) was added thereto, and the mixture was refluxed for 30 minutes. After cooling, the solvent was removed in vacuo, and the residue was dissolved in ethyl acetate. Insoluble material was filtered off, and the filtrate was washed with saturated sodium bicarbonate solution, water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1, v/v) to give ethyl N-(3-methoxy-2-nitrophenyl)carbamate (7.23 g).

Workup

  1. temperaturewas refluxed for 40 minutes
  2. temperaturethe mixture was refluxed for 30 minutes
  3. temperatureAfter cooling
  4. customthe solvent was removed in vacuo
  5. dissolutionthe residue was dissolved in ethyl acetate
  6. filtrationInsoluble material was filtered off
  7. washthe filtrate was washed with saturated sodium bicarbonate solution, water and brine
  8. dry with materialdried over magnesium sulfate
  9. customevaporated in vacuo
  10. customThe residue was purified by silica gel column chromatography (hexane

Sources & evidence

ORD record
ord-ee66fee67fcd4e1d94de1e5072567073
Source dataset
uspto-grants-2000_07
Patent number
US06083961

Reaction notes

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