Triethylamine → HCID 178466049, compound

HRID 523096Notes

Reaction equation

HRID 523096 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1[N+:14]([O-:16])=[O:15])[C:7]([NH:9][NH2:10])=O)[CH3:2].[CH3:17][N:18]=[C:19]=[S:20].C(N(CC)CC)C>C1COCC1>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:7]2[N:18]([CH3:17])[C:19]([SH:20])=[N:10][N:9]=2)[CH:11]=[CH:12][C:13]=1[N+:14]([O-:16])=[O:15])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11167Methyl isothiocyanateHCID 899955863-Ethoxy-4-nitrobenzohydrazide

Product 1

HCID 178466049HCID 178466049, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
20 °C

Procedure

3-Ethoxy-4-nitrobenzohydrazide (Preparation 118, 1287 mg 5.72 mmole) was stirred in THF (26 mL) and a solution of methyl isothiocyanate (422 mg 5.78 mmole) in THF (5 mL) was added. Triethylamine (102 uL, 0.71 mmole) was added and the reaction was stirred at 20° C. for 22 hours. The solvent was evaporated and replaced with 1M sodium hydroxide solution (85 mL) and the reaction was stirred at 45° C. for 2.5 hours. The reaction was filtered through Celite and the filtrate extracted with ether (2×45 mL). The aqueous was acidified using conc. hydrochloric acid and extracted with ethyl acetate (2×50 mL). The combined ethyl acetate extracts were washed with water and with brine, dried over sodium sulfate and concentrated in vacuo to afford the title compound (1.16 g, 72%).

Workup

  1. customThe solvent was evaporated
  2. stirringthe reaction was stirred at 45° C. for 2.5 hours
  3. filtrationThe reaction was filtered through Celite
  4. extractionthe filtrate extracted with ether (2×45 mL)
  5. extractionextracted with ethyl acetate (2×50 mL)
  6. washThe combined ethyl acetate extracts were washed with water and with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-25c4dff6bfde46d58b112a4ba70866fd
Source dataset
uspto-grants-2016_05
Patent number
US09334286B2

Reaction notes

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