Carbon Disulfide → HCID 178519452, compound

HRID 1025916Notes

Reaction equation

HRID 1025916 reaction equation
[OH:1][CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([NH:9][NH2:10])=[O:8])=[CH:5][CH:4]=1.[C:13](=S)=[S:14].C(N(CC)CC)C>C(O)C.C(OCC)(=O)C>[SH:14][C:13]1[O:8][C:7]([C:6]2[CH:11]=[CH:12][C:3]([CH2:2][OH:1])=[CH:4][CH:5]=2)=[N:9][N:10]=1

Participants

6

Reactant 3

HCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 432368204-(Hydroxymethyl)benzohydrazide

Product 1

HCID 178519452HCID 178519452, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(hydroxymethyl)benzoic hydrazide CAS [58855-42-8] (1.4 g, 8.4 mmol) in ethanol (14 mL) were added carbon disulfide (1.12 mL, 18.5 mmol) and triethyl amine (1.3 mL, 9.3 mmol). After heating to reflux for 16 h with stirring, the reaction mixture was cooled to RT and diluted with ethyl acetate. The mixture was washed with 10% HCl solution and brine, dried over magnesium sulfate, and concentrated. Purification of the residue by MPLC (65% ethyl acetate in hexanes) gave 1.62 g of [4-(5-mercapto-1,3,4-oxadiazol-2-yl)phenyl]methanol as a colorless solid. 1H NMR (600 MHz, CD3OD) δ 7.90 (ddd, J=0.59, 2.05, 8.51 Hz, 2H), 7.54 (d, J=7.92 Hz, 2H), 4.68 (s, 2H)

Workup

  1. temperatureAfter heating
  2. temperatureto reflux for 16 h
  3. washThe mixture was washed with 10% HCl solution and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customPurification of the residue by MPLC (65% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-b78c67e03be74cbf850023fcec916aee
Source dataset
uspto-grants-2014_05
Patent number
US08729110B1

Reaction notes

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