Ethanol → HCID 178527970, compound

HRID 732030Notes

Reaction equation

HRID 732030 reaction equation
[CH:1]([NH:3][NH2:4])=O.[N:5]([CH2:8][C:9]1[O:10][CH:11]=[CH:12][CH:13]=1)=[C:6]=[S:7].C(O)C>N1C=CC=CC=1>[O:10]1[CH:11]=[CH:12][CH:13]=[C:9]1[CH2:8][N:5]1[CH:1]=[N:3][N:4]=[C:6]1[SH:7]

Participants

5

Reactant 3

HCID 702EthanolHCID 12229HydrazinecarboxaldehydeHCID 783802-(Isothiocyanatomethyl)furan

Product 1

HCID 178527970HCID 178527970, compoundYield 83.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A solution of formic acid hydrazide (439 mg, 7.809 mmol) in pyridine (20 ml) was added to a solution of 2-isothiocyanatomethyl-furan (1 g, 7.185 mmol) in pyridine (20 ml). Reaction took place at room temperature overnight, and ethanol (20 ml) was added directly to the reaction and placed in 80C bath overnight. Solvent was evaporated and the title compound (1.09 g, 83%) was obtained from purification by SPE chromatography on silica gel with 500 ml 20%, 250 ml 25%, 250 ml 30%, 250 ml 35%, 250 ml 40%, and 250 ml 50% ethyl acetate in hexanes. 1H NMR (CD3OD), δ (ppm): 14.0 (bs, 1H), 8.19 (s, 1H), 7.52 (q, 1H), 6.52 (m, 1H), 6.42 (m, 1H), 4.90 (s, 2H).

Workup

  1. customReaction
  2. customat room temperature
  3. additionwas added directly to the reaction
  4. customSolvent was evaporated

Sources & evidence

ORD record
ord-fddb11e2fa3d415cbcf778f8e2af7f3b
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

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