4-Nitrobenzoyl chloride → HCID 86598615, compound

HRID 1817132Notes

Reaction equation

HRID 1817132 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-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 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-bae92dcb78ac4aedaae89e7b263fa1cf
Source dataset
uspto-grants-2009_10
Patent number
US07598232B2

Reaction notes

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