4-Fluorobenzaldehyde → HCID 501542, compound

HRID 2086913Notes

Reaction equation

HRID 2086913 reaction equation
[C:1]1([S:7]([NH:10][N:11]2[C:15](=[O:16])[CH2:14][S:13][C:12]2=[S:17])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=1.CC([O-])=O.[Na+]>CO>[F:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=[C:14]2[S:13][C:12](=[S:17])[N:11]([NH:10][S:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)(=[O:9])=[O:8])[C:15]2=[O:16])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 680234-FluorobenzaldehydeHCID 402431HCID 402431, compoundHCID 517045Sodium Acetate

Product 1

HCID 501542HCID 501542, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-(Benzenesulfonylamino)-4-oxo-2-thionothiazolidine 624 mg (2.17 mmol, 1.0 equiv) was combined with 349 μL 4-fluorobenzaldehyde (3.26 mmol, 1.5 equiv) and 18 mg NaOAc (0.217 mmol, 0.1 equiv) in 8 mL MeOH. The solution was allowed to stir for 5 h, at which time the resulting yellow solid was removed via filtration. The solid was washed (4×MeOH) and dried under vacuum to give the product as a yellow solid 83.5 mg (0.212 mmol, 10%). 1H NMR (DMSO, 400 MHz) δ 7.90-9.86 (m, 3 H), 7.77-7.70 (m, 3 H), 7.61 (t, J=8.8 Hz, 2 H), 7.42 (t, J=8.8 Hz, 2 H).

Workup

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

Sources & evidence

ORD record
ord-952e1a95474e4aeba7d52723f0fdb226
Source dataset
uspto-grants-2004_04
Patent number
US06727267B2

Reaction notes

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