Bromomethyl acetate → HCID 178476666, compound

HRID 353692Notes

Reaction equation

HRID 353692 reaction equation
[CH3:1][N:2]([CH3:33])[C:3]1[CH:4]=[CH:5][C:6]2[C:15]([CH:16]=1)=[O+:14][C:13]1[C:8](=[CH:9][CH:10]=[C:11]([N:17]([CH3:19])[CH3:18])[CH:12]=1)[C:7]=2[C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[C:22]([NH2:29])[C:21]=1[C:30]([OH:32])=[O:31].C(N(C(C)C)CC)(C)C.[C:43]([O:46][CH2:47][Br:48])(=[O:45])[CH3:44]>ClC(Cl)C>[Br-:48].[CH3:1][N:2]([CH3:33])[C:3]1[CH:4]=[CH:5][C:6]2[C:15]([CH:16]=1)=[O+:14][C:13]1[C:8](=[CH:9][CH:10]=[C:11]([N:17]([CH3:18])[CH3:19])[CH:12]=1)[C:7]=2[C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[C:22]([NH2:29])[C:21]=1[C:30]([O:32][CH2:47][O:46][C:43](=[O:45])[CH3:44])=[O:31]

Participants

5

Reactant 3

HCID 68536Bromomethyl acetate2×HCID 81531Diisopropylethylamine2×HCID 178482590HCID 178482590, compound

Product 1

HCID 178476666HCID 178476666, compoundYield 13.6%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent2×

Procedure

3,6-Bis(dimethylamino)-9-(3-amino-2-carboxy-4-nitrophenyl)xanthylium intramolecular salt (2.44 g) prepared by the method disclosed in WO99/01447 was dissolved in 120 ml of dichloroethane, and the solution was added with 1 ml of diisopropylethylamine. The mixture was further added with acetoxymethyl bromide (0.55 ml), and stirred at room temperature. The progress of the reaction was monitored every day by TLC, and additional diisopropylethylamine and acetoxymethyl bromide were added in amounts half of those used for the first addition. After 4 days, the reaction mixture was added with dichloroethane and washed with water, and the solvent was evaporated. The residue was purified by silica gel column chromatography to obtain 3,6-bis(dimethylamino)-9-(2-acetoxymethoxycarbonyl-3-amino-4-nitrophenyl)xanthylium bromide (0.445 g, 13.6%).

Workup

  1. additionwere added in amounts half of
  2. additionthose used for the first addition
  3. washwashed with water
  4. customthe solvent was evaporated
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-48ddede0ae05446cbeb3cbcaff4be2a7
Source dataset
uspto-grants-2004_06
Patent number
US06756231B1

Reaction notes

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