Ammonia → HCID 22929828, compound

HRID 1295992Notes

Reaction equation

HRID 1295992 reaction equation
[N:1]([CH2:4][C:5]1[C:13]([C:14]#N)=[CH:12][C:8](C(O)=O)=[C:7]([O:16][CH2:17][CH3:18])[CH:6]=1)=[N+:2]=[N-:3].C([N:21]([CH2:24][CH3:25])CC)C.ClC(OCC)=[O:28].N>O1CCCC1.C(OCC)(=O)C.O>[N:1]([CH2:4][C:5]1[C:13]([C:12]#[CH:8])=[CH:14][C:25]([C:24]([NH2:21])=[O:28])=[C:7]([O:16][CH2:17][CH3:18])[CH:6]=1)=[N+:2]=[N-:3]

Participants

8

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 22929650HCID 22929650, compound

Product 1

HCID 22929828HCID 22929828, compoundYield 97.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

After dissolving 4-(azidomethyl)-5-cyano-2-ethoxybenzoic acid (0.7 g, 2.85 mmol) in tetrahydrofuran (15 ml), triethylamine (0.48 ml, 3.42 mmol) and ethyl chloroformate (0.3 ml, 3.14 mmol) were added while cooling on ice. The mixture was stirred for 10 minutes while cooling on ice, and then 27% aqueous ammonia (10 ml) was added and the mixture was stirred at room temperature for 10 minutes. Water (30 ml) was added to the reaction mixture, extraction was performed with ethyl acetate (20 ml×3), and then after washing the combined organic layers with brine (30 ml) and drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The obtained crude product (0.68 g) was used directly for the following reaction.

Workup

  1. additionwere added
  2. temperaturewhile cooling on ice
  3. temperaturewhile cooling on ice
  4. stirringthe mixture was stirred at room temperature for 10 minutes
  5. washafter washing the combined organic layers with brine (30 ml)
  6. dry with materialdrying over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-3bc3781e237c484dad41e346484cd2f2
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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