4-Nitrobenzoyl chloride → HCID 86598615, compound

HRID 2188732Notes

Reaction equation

HRID 2188732 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:13][O:14][C:15]1[CH:59]=[C:58]([O:60][CH3:61])[CH:57]=[C:56]([O:62][CH3:63])[C:16]=1[CH:17]=[CH:18][CH:19]([S:29]([CH:32]([CH:42]=[CH:43][C:44]1[C:49]([O:50][CH3:51])=[CH:48][C:47]([O:52][CH3:53])=[CH:46][C:45]=1[O:54][CH3:55])[C:33]1[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[C:35]([NH2:41])[CH:34]=1)(=[O:31])=[O:30])[C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([NH2:28])[CH:21]=1>O1CCCC1>[CH3:63][O:62][C:56]1[CH:57]=[C:58]([O:60][CH3:61])[CH:59]=[C:15]([O:14][CH3:13])[C:16]=1/[CH:17]=[CH:18]/[CH:19]([S:29]([CH:32](/[CH:42]=[CH:43]/[C:44]1[C:45]([O:54][CH3:55])=[CH:46][C:47]([O:52][CH3:53])=[CH:48][C:49]=1[O:50][CH3:51])[C:33]1[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[C:35]([NH:41][C:8](=[O:9])[C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=2)[CH:34]=1)(=[O:31])=[O:30])[C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([NH:28][C:8](=[O:9])[C:7]2[CH:11]=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[CH:21]=1

Participants

4

Reactant 2

HCID 85024-Nitrobenzoyl chlorideHCID 66912535HCID 66912535, compound

Product 1

HCID 86598615HCID 86598615, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-nitrobenzoyl chloride (10 mmol) in tetrahydrofuran (40 mL) was added dropwise a solution of 2,4,6-trimethoxystyryl-3-amino-4-methoxy-benzylsulfone (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 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-(4-nitrobenzamido)-4-methoxybenzylsulfone in 72% yield. m.p. 206-208° C. NMR (DMSO-d6) δ 3.80 (s, 3H), 3.81 (s, 6H), 3.83 (s, 3H), 4.18 (s, 2H), 6.08 (s, 2H), 7.14-7.23 (d, 1H vinylic), 6.97-7.86 (m, aromatic), 9.05 (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-e6217b2e3b36474abf82c24e81bc4eed
Source dataset
uspto-grants-2012_12
Patent number
US08324190B2

Reaction notes

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