Dimethyl Sulfate → HCID 22364788, compound

HRID 1781636Notes

Reaction equation

HRID 1781636 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:14])[C:5](=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[C:6]([OH:8])=[O:7].[OH-].[CH2:16]([N+](CCCC)(CCCC)CCCC)CCC.S(OC)(OC)(=O)=O>ClCCl>[CH3:16][O:7][C:6](=[O:8])[C:5]1[C:4](=[CH:3][C:2]([Cl:1])=[CH:10][C:9]=1[N+:11]([O-:13])=[O:12])[NH2:14]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 2723671Tetrabutylammonium HydroxideHCID 190467352-Amino-4-chloro-6-nitrobenzoic acid

Product 1

HCID 22364788HCID 22364788, compoundYield 48.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3.25 g (15 mmol) of 4-chloro-6-nitro-anthranilic acid and 9.73 ml of a 40% aqueous solution of tetrabutylammonium hydroxide are placed in 65 ml of dichloromethane. Then 1.43 ml (15 mmol) of dimethyl sulfate are added dropwise thereto and the mixture is stirred for 1 hour at room temperature and washed in succession with a small amount of water and saturated sodium chloride solution. The aqueous phases are extracted by shaking with dichloromethane and the combined organic phases are dried over sodium sulfate, filtered and concentrated. The residue is stirred with a small amount of ethyl acetate. The product is precipitated with hexane and dried. 1.67 g (48.3% of theory) of 4-chloro-6-nitro-anthranilic acid methyl ester having a melting point of 114°-116° are obtained.

Workup

  1. washwashed in succession with a small amount of water and saturated sodium chloride solution
  2. extractionThe aqueous phases are extracted
  3. stirringby shaking with dichloromethane
  4. dry with materialthe combined organic phases are dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. stirringThe residue is stirred with a small amount of ethyl acetate
  8. customThe product is precipitated with hexane
  9. customdried

Sources & evidence

ORD record
ord-d7c0badf483346398413ee261ac19298
Source dataset
uspto-grants-1997_05
Patent number
US05633379

Reaction notes

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