Ethanol → HCID 14207583, compound

HRID 1252726Notes

Reaction equation

HRID 1252726 reaction equation
[NH2:1][C:2]1[C:12]([CH3:13])=[C:11]([N+:14]([O-:16])=[O:15])[CH:10]=[C:9]([CH2:17][CH3:18])[C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].Cl[C:20]([O:22][C:23](Cl)(Cl)Cl)=[O:21].[CH2:27](O)C.C(N(CC)CC)C>O1CCCC1>[CH2:17]([C:9]1[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])=[C:2]([NH:1][C:20]([O:22][CH2:23][CH3:27])=[O:21])[C:12]([CH3:13])=[C:11]([N+:14]([O-:16])=[O:15])[CH:10]=1)[CH3:18]

Participants

6

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 10426DiphosgeneHCID 14207582HCID 14207582, compound

Product 1

HCID 14207583HCID 14207583, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of ethyl 2-amino-3-methyl-6-ethyl-4-nitro-benzoate (70 mg, 0.000277 mol) in anhydrous tetrahydrofuran (5 ml) was added slowly to a solution of trichloromethyl chloroformate (43 mg) in tetrahydrofuran (5 ml). The solution was stirred for 2 hrs. at room temperature and then added slowly to a solution of ethanol (1 ml), triethylamine (0.05 ml) in tetrahydrofuran (5 ml). The resulting mixture was sitirred for 2 hrs. and evaporated to dryness. The residue was partitioned between ethyl acetate and water. The organic layer was dried over magnesium sulphate and evaporated to dryness. This material was purified by thick layer plate chromatography to yield ethyl 6-ethyl-3-methyl-2-ethoxycarbonylamino-4-nitrobenzoate. Yield: 35 mg, IR (CHCl3): 3420, 1730, 1530, 1500 cm-1. H-NMR: 1.10-1.50 (overlapping peaks [3t], 9H, CH3CH2, CH3CH2O, CH3CH2O), 2.31 (s, 3H, CH3), 2.70 (q, 2H, CH3CH2Ar), 4.20 (q, 2H, CH2O), 4.40, (q, 2H, CH2O), 6.60 (br.s, 1H, NH), 7.69 (s, 1H, ArH).

Workup

  1. waitThe resulting mixture was sitirred for 2 hrs
  2. customand evaporated to dryness
  3. customThe residue was partitioned between ethyl acetate and water
  4. dry with materialThe organic layer was dried over magnesium sulphate
  5. customevaporated to dryness
  6. customThis material was purified by thick layer plate chromatography

Sources & evidence

ORD record
ord-3bb05487969e4926ab427b6c19055808
Source dataset
uspto-grants-1988_05
Patent number
US04745116

Reaction notes

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