Ethanol → HCID 178527970, compound

HRID 273119Notes

Reaction equation

HRID 273119 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 80 C 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. customplaced in 80 C bath overnight
  5. customSolvent was evaporated

Sources & evidence

ORD record
ord-5fb7e3f92e2c429ebb7d6b2cb53be659
Source dataset
uspto-grants-2008_11
Patent number
US07456200B2

Reaction notes

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