3,5-Dinitrobenzoyl chloride → HCID 86598611, compound

HRID 2188727Notes

Reaction equation

HRID 2188727 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=1)[C:7](Cl)=[O:8])([O-:3])=[O:2].[CH3:16][O:17][C:18]1[CH:62]=[C:61]([O:63][CH3:64])[CH:60]=[C:59]([O:65][CH3:66])[C:19]=1[CH:20]=[CH:21][CH:22]([S:32]([CH:35]([CH:45]=[CH:46][C:47]1[C:52]([O:53][CH3:54])=[CH:51][C:50]([O:55][CH3:56])=[CH:49][C:48]=1[O:57][CH3:58])[C:36]1[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[C:38]([NH2:44])[CH:37]=1)(=[O:34])=[O:33])[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([NH2:31])[CH:24]=1>O1CCCC1>[CH3:66][O:65][C:59]1[CH:60]=[C:61]([O:63][CH3:64])[CH:62]=[C:18]([O:17][CH3:16])[C:19]=1/[CH:20]=[CH:21]/[CH:22]([S:32]([CH:35](/[CH:45]=[CH:46]/[C:47]1[C:48]([O:57][CH3:58])=[CH:49][C:50]([O:55][CH3:56])=[CH:51][C:52]=1[O:53][CH3:54])[C:36]1[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[C:38]([NH:44][C:7](=[O:8])[C:6]2[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=2)[CH:37]=1)(=[O:34])=[O:33])[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([NH:31][C:7](=[O:8])[C:6]2[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=2)[CH:24]=1

Participants

4

Reactant 2

HCID 74323,5-Dinitrobenzoyl chlorideHCID 66912535HCID 66912535, compound

Product 1

HCID 86598611HCID 86598611, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3,5-dinitrobenzoyl chloride (10 mmol) in tetrahydrofuran (40 mL) was added drop wise 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-(3,5-dinitrobenzamido)-4-methoxy-benzylsulfone in 80% yield (m.p. 277-279° C.). NMR (DMSO-d6) δ 3.80 (s, 3H), 3.82 (s, 6H), 3.86 (s, 3H), 4.35 (s, 2H), 6.3 (s, 2H), 7.15-9.1 (m, aromatic+vinylic), 9.8 (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-e88d5f4fd91c42c7aad0ebe26a82c09a
Source dataset
uspto-grants-2012_12
Patent number
US08324190B2

Reaction notes

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