Acetyl chloride → HCID 86635767, compound

HRID 1817135Notes

Reaction equation

HRID 1817135 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[CH3:5][O:6][C:7]1[CH:51]=[C:50]([O:52][CH3:53])[CH:49]=[C:48]([O:54][CH3:55])[C:8]=1[CH:9]=[CH:10][CH:11]([S:21]([CH:24]([CH:34]=[CH:35][C:36]1[C:41]([O:42][CH3:43])=[CH:40][C:39]([O:44][CH3:45])=[CH:38][C:37]=1[O:46][CH3:47])[C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([NH2:33])[CH:26]=1)(=[O:23])=[O:22])[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([NH2:20])[CH:13]=1.[O:56]1CC[CH2:58][CH2:57]1>>[CH3:55][O:54][C:48]1[CH:49]=[C:50]([O:52][CH3:53])[CH:51]=[C:7]([O:6][CH3:5])[C:8]=1/[CH:9]=[CH:10]/[CH:11]([S:21]([CH:24](/[CH:34]=[CH:35]/[C:36]1[C:37]([O:46][CH3:47])=[CH:38][C:39]([O:44][CH3:45])=[CH:40][C:41]=1[O:42][CH3:43])[C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([NH:33][C:57](=[O:56])[CH3:58])[CH:26]=1)(=[O:23])=[O:22])[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([NH:20][C:1](=[O:3])[CH3:2])[CH:13]=1

Participants

4

Reactant 3

HCID 6367Acetyl chlorideHCID 8028Tetrahydrofuran2×HCID 66912535HCID 66912535, compound

Product 1

HCID 86635767HCID 86635767, compoundYield 68%

Procedure

To a solution of acetyl chloride (10 mmol) in tetrahydrofuran (40 mL) was added dropwise a solution of 2,4,6-trimethoxystyryl-3-amino-4-methoxybenzylsulfone (10 mmol) in tetrahydrofuran. The solution was stirred overnight and the completion of the reaction was monitored by TLC. The solvent was removed and the residue was taken up in dichloromethane and washed with water. The organic layer was dried over anhydrous sodium sulfate and evaporated to give (E)-2,4,6-trimethoxystyryl-3-(acetamido)-4-methoxybenzylsulfone in 68% yield. M.p. 220-223° C. NMR (DMSO-d6) δ 2.02(s, 2H), 3.84(s, 3H), 3.86(s, 6H), 3.88(s, 3H), 4.22 (s, 2H), 6.08(s, 2H), 7.09-7.12(d, 1H vinylic), 6.88-7.86(m, aromatic), 8.35(s, 1H).

Workup

  1. customThe solvent was removed
  2. washwashed with water
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-4a6f1ee3eb014fe597eccb106cc0eb4b
Source dataset
uspto-grants-2009_10
Patent number
US07598232B2

Reaction notes

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