Dimethyl Sulfate → HCID 11300689, compound

HRID 1241690Notes

Reaction equation

HRID 1241690 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=2[C:11]([OH:13])=O)[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].S(OC)(O[CH3:24])(=O)=O>S(=O)(=O)(O)O.CN(C=O)C.O.C(O)(=O)C>[Br:1][C:2]1[C:3]2[C:11](=[O:13])[C:10]3[C:9](=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:8]([CH3:24])[C:4]=2[CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 3

HCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 149524612-(3-Bromoanilino)benzoic acid2×

Product 1

HCID 11300689HCID 11300689, compoundYield 26%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

(Method E-1) 2-(3-Bromo-phenylamino)benzoic acid, 13 (9.5 g, 32.5 mmol) was dissolved in conc. sulphuric acid (50 ml) and heated to 100° C. for 40 mins. After cooling, water was added slowly giving a green solid. The solid was filtered off and washed with water, and dried over phosphorous pentoxide. The crude material was partially dissolved in DMF (100 ml) and slowly added under nitrogen to sodium hydride (3.75 g, 156 mmol) in DMF (50 ml), and the mixture stirred for 30 mins. Dimethyl sulphate (12 ml, 72 mmol) was added and stirring continued for a further 30 mins before adding acetic acid (1 ml), then water (400 ml). The precipitate was filtered off, and the crude mix of 1 and 3-bromo acridones separated by column chromatography to give the title compound (2.43 g, 8.86 mmol, 26% over 2 steps). See, for example, Hodgeman et al., 1972.

Workup

  1. temperatureAfter cooling
  2. customgiving a green solid
  3. filtrationThe solid was filtered off
  4. washwashed with water
  5. dry with materialdried over phosphorous pentoxide
  6. dissolutionThe crude material was partially dissolved in DMF (100 ml)
  7. stirringstirring
  8. waitcontinued for a further 30 mins
  9. filtrationThe precipitate was filtered off
  10. additionthe crude mix of 1 and 3-bromo acridones
  11. customseparated by column chromatography

Sources & evidence

ORD record
ord-95efac1897a9493aad165ca19f698252
Source dataset
uspto-grants-2006_10
Patent number
US07115619B2

Reaction notes

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