3,4-Dichlorobenzaldehyde → HCID 501594, compound

HRID 2086914Notes

Reaction equation

HRID 2086914 reaction equation
[CH3:1][S:2]([NH:5][N:6]1[C:10](=[O:11])[CH2:9][S:8][C:7]1=[S:12])(=[O:4])=[O:3].[Cl:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][C:21]=1[Cl:22])[CH:17]=O.CC([O-])=O.[Na+]>CO>[Cl:13][C:14]1[CH:15]=[C:16]([CH:17]=[C:9]2[S:8][C:7](=[S:12])[N:6]([NH:5][S:2]([CH3:1])(=[O:4])=[O:3])[C:10]2=[O:11])[CH:19]=[CH:20][C:21]=1[Cl:22]

Participants

5

Reactant 3

HCID 227103,4-DichlorobenzaldehydeHCID 517045Sodium AcetateHCID 11535929HCID 11535929, compound

Product 1

HCID 501594HCID 501594, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-(Methanesulfonylamino)-4-oxo-2-thionothiazolidine 269 mg (1.19 mmol, 1.0 equiv) was dissolved in 3 mL MeOH followed by the addition of 208 mg 3,4-dichlorobenzaldehyde (1.19 mmol, 1.0 equiv) and 10 mg NaOAc (0.119 mmol, 0.1 equiv). The solution was allowed to stir for 24 hours, at which time the yellow solid was removed by filtration. The solid was washed (4×MeOH) and dried under vacuum to give the 248 mg of the product as a yellow solid (0.649 mmol, 55%). 1H NMR (DMSO, 400 MHz) δ 8.01 (d, J=1.0 Hz, 1 H), 7.95 (s, 1 H), 7.84 (d, J=8.4 Hz, 1 H), 7.63 (dd, J=2.1, 8.4 Hz, 1 H), 3.28 (s, 3 H).

Workup

  1. customwas removed by filtration
  2. washThe solid was washed (4×MeOH)
  3. customdried under vacuum

Sources & evidence

ORD record
ord-360fa05ab80b448fb678a5d3031b51d7
Source dataset
uspto-grants-2004_04
Patent number
US06727267B2

Reaction notes

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