Trimethylamine → HCID 21099927, compound

HRID 1352176Notes

Reaction equation

HRID 1352176 reaction equation
[CH:1]([C:4]1[CH:31]=[CH:30][C:7]([NH:8][C:9]2[CH:10]=[CH:11][C:12]([OH:29])=[C:13]3[C:22]=2[C:21](=[O:23])[C:20]2[C:19]([OH:24])=[CH:18][CH:17]=[C:16]([N+:25]([O-:27])=[O:26])[C:15]=2[C:14]3=[O:28])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[S:32](Cl)([C:35]1[CH:41]=[CH:40][C:38]([CH3:39])=[CH:37][CH:36]=1)(=[O:34])=[O:33].CN(C)C>ClCCl>[CH:1]([C:4]1[CH:31]=[CH:30][C:7]([NH:8][C:9]2[CH:10]=[CH:11][C:12]([O:29][S:32]([C:35]3[CH:41]=[CH:40][C:38]([CH3:39])=[CH:37][CH:36]=3)(=[O:34])=[O:33])=[C:13]3[C:22]=2[C:21](=[O:23])[C:20]2[C:19]([O:24][S:32]([C:35]4[CH:41]=[CH:40][C:38]([CH3:39])=[CH:37][CH:36]=4)(=[O:34])=[O:33])=[CH:18][CH:17]=[C:16]([N+:25]([O-:27])=[O:26])[C:15]=2[C:14]3=[O:28])=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1146TrimethylamineHCID 73974-Toluenesulfonyl chlorideHCID 21099926HCID 21099926, compound

Product 1

HCID 21099927HCID 21099927, compoundYield 95.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 1.2 g of 8-(4′-isopropylanilino)-1,5-dihydroxy-4-nitroanthraquinone and a 1.4 g of tosyl chloride were dissolved in 20 ml of dichloromethane, and a 1.0 ml of trimethylamine was added to the solution and allowed to react for 12 hours at room temperature under stirring. The reaction solution was extracted with adequate amounts of ethyl acetate and 1N-hydrochloric acid to separate into two layers. The extracted organic layer was dried with magnesium sulfate and concentrated. The obtained product was purified by silica gel chromatography to give a 2.0 g of 8-(4′-isopropylanilino)-4-nitro-1,5-bis(p-toluenesulfonyloxy)anthraquinone in a 94% yield.

Workup

  1. customto react for 12 hours at room temperature
  2. extractionThe reaction solution was extracted with adequate amounts of ethyl acetate and 1N-hydrochloric acid
  3. customto separate into two layers
  4. dry with materialThe extracted organic layer was dried with magnesium sulfate
  5. concentrationconcentrated
  6. customThe obtained product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-4a9cafc164254acea8606180d11c208d
Source dataset
uspto-grants-2007_05
Patent number
US07220465B2

Reaction notes

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