Chloroacetyl chloride → HCID 66912773, compound

HRID 2188729Notes

Reaction equation

HRID 2188729 reaction equation
[CH3:1][O:2][C:3]1[CH:47]=[C:46]([O:48][CH3:49])[CH:45]=[C:44]([O:50][CH3:51])[C:4]=1[CH:5]=[CH:6][CH:7]([S:17]([CH:20]([CH:30]=[CH:31][C:32]1[C:37]([O:38][CH3:39])=[CH:36][C:35]([O:40][CH3:41])=[CH:34][C:33]=1[O:42][CH3:43])[C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([NH2:29])[CH:22]=1)(=[O:19])=[O:18])[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([NH2:16])[CH:9]=1.[Cl:52][CH2:53][C:54](Cl)=[O:55]>C1(C)C=CC=CC=1.O1CCOCC1>[CH3:51][O:50][C:44]1[CH:45]=[C:46]([O:48][CH3:49])[CH:47]=[C:3]([O:2][CH3:1])[C:4]=1[CH:5]=[CH:6][CH:7]([S:17]([CH:20]([CH:30]=[CH:31][C:32]1[C:33]([O:42][CH3:43])=[CH:34][C:35]([O:40][CH3:41])=[CH:36][C:37]=1[O:38][CH3:39])[C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([NH:29][C:54](=[O:55])[CH2:53][Cl:52])[CH:22]=1)(=[O:19])=[O:18])[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([NH:16][C:54](=[O:55])[CH2:53][Cl:52])[CH:9]=1

Participants

5

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 66912535HCID 66912535, compound

Product 1

HCID 66912773HCID 66912773, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2,4,6-trimethoxystyryl-3-amino-4-methoxybenzylsulfone (10 mmol) in toluene, chloroacetyl chloride (10 mmol) in dioxane (10 mL) was added and the solution was refluxed for 2 h. The solution was cooled and the solvent was removed in a rotary evaporator to give 2,4,6-trimethoxystyryl-3-chloroacetamido-4-methoxybenzylsulfone in 88% yield. M.p. 163-165° C. NMR (DMSO-d6) δ 3.83 (s, 3H), 3.84 (s, 6H), 3.85 (s, 3H), 4.14 (s, 2H), 4.22 (s, 2H) 6.08 (s, 2H), 7.11-7.20 (d, 1H vinylic), 6.90-8.33 (m, aromatic), 8.89 (s, 1H).

Workup

  1. temperaturethe solution was refluxed for 2 h
  2. temperatureThe solution was cooled
  3. customthe solvent was removed in a rotary evaporator

Sources & evidence

ORD record
ord-06971a8b24c746e69d0646cb5d65b4c6
Source dataset
uspto-grants-2012_12
Patent number
US08324190B2

Reaction notes

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