Thiosemicarbazide → 3-[3-(2-Methoxyphenylsulfonyloxy)-5-methylphenoxy]propionaldehyde thiosemicarbazone

HRID 442987Notes

Reaction equation

HRID 442987 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([O:12][C:13]1[CH:14]=[C:15]([CH:21]=[C:22]([CH3:24])[CH:23]=1)[O:16][CH2:17][CH2:18][CH:19]=O)(=[O:11])=[O:10].[NH2:25][NH:26][C:27]([NH2:29])=[S:28]>C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([O:12][C:13]1[CH:14]=[C:15]([CH:21]=[C:22]([CH3:24])[CH:23]=1)[O:16][CH2:17][CH2:18][CH:19]=[N:25][NH:26][C:27]([NH2:29])=[S:28])(=[O:11])=[O:10]

Participants

4

Reactant 2

HCID 2723789ThiosemicarbazideHCID 227226443-[3-(2-Methoxyphenylsulfonyloxy)-5-methylphenoxy]propionaldehyde

Product 1

HCID 541667873-[3-(2-Methoxyphenylsulfonyloxy)-5-methylphenoxy]propionaldehyde thiosemicarbazone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-[3-(2-methoxyphenylsulfonyloxy)-5-methylphenoxy-]-propionaldehyde (472.5 mg, 1.35 mmol, as prepared in step d of example 8), thiosemicarbazide (124.5 mg, 1.37 mmol) and ethanol (4.5 mL) was refluxed for 2 hours. The solution was cooled to room temperature and approximately 3 mL ethanol was removed by rotary evaporation. The residual oil in ethanol was heated to 50° C. and the product crystallized. The title compound was isolated by filtration as a white solid (493 mg, 86%). 1H-NMR (300 MHz, DMSO-d6) δ 7.76 (ddd, 1H, J=1.8, 7.4, 8.4 Hz), 7.69 (dd, 1H, J=1.7, 7.9 Hz), 7.43 (t, 1H, J=4.8 Hz), 7.36 (d, 1H, J=8.4 Hz), 7.09 (ddd, 1H, J=0.9, 7.4, 7.8 Hz), 6.72 (br s, 1H), 6.48 (br s, 1H), 6.37 (t, 1H, J=2.3 Hz), 4.08 (t, 2H, J=6.5 Hz), 3.99 (s, 3H), 2.58 (q, 2H, J=6.4 Hz), 2.21 (s, 3H). Mass spectrum (MALDI-TOF, α-cyano-4-hydroxycinnamic acid matrix) calcd. for C18H21N3O5S2 : 424.1 (M+H), 446.1 (M+Na). Found: 423.9, 445.9.

Workup

  1. temperaturewas refluxed for 2 hours
  2. customapproximately 3 mL ethanol was removed by rotary evaporation
  3. temperatureThe residual oil in ethanol was heated to 50° C.
  4. customthe product crystallized

Sources & evidence

ORD record
ord-58159d417d5442aa8a33334c429e4d4f
Source dataset
uspto-grants-1999_04
Patent number
US05891909

Reaction notes

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