Methyl 4-chloroanthranilate → HCID 57576651, compound

HRID 555923Notes

Reaction equation

HRID 555923 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(N(C(C)C)CC)(C)C.[Cl:22][C:23]1[CH:27]=[CH:26][S:25][C:24]=1[C:28](Cl)=[O:29]>ClCCl.CN(C)C=O>[Cl:12][C:10]1[CH:9]=[CH:8][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([NH:1][C:28]([C:24]2[S:25][CH:26]=[CH:27][C:23]=2[Cl:22])=[O:29])[CH:11]=1

Participants

6

Reactant 3

HCID 80001Methyl 4-chloroanthranilateHCID 81531DiisopropylethylamineHCID 27358243-Chlorothiophene-2-carbonyl chloride

Product 1

HCID 57576651HCID 57576651, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Methyl 2-amino-4-chlorobenzoate (200 mg, 1.1 mmol) and diisopropylethylamine (285 μL, 1.6 mmol) were dissolved in a solution of dichloromethane (4 mL) and dimethylformamide (2 mL). 3-Chlorothiophene-2-carbonyl chloride (235 mg, 1.3 mmol) was added dropwise. The reaction mixture was stirred overnight at room temperature. The solvent was removed under vacuum and the residue was re-dissolved in 25 mL of ethyl acetate. The reaction mixture was washed one time each with 10 mL portions of water, 0.1 M NaOH, and saturated aqueous NaCl. The organic layer was dried with MgSO4 and 90 mg of solid was precipitated by the addition of hexanes. The material was used without further purification. MS (EI) for C13H9Cl2NO3S: 330 (M+H).

Workup

  1. customThe solvent was removed under vacuum
  2. dissolutionthe residue was re-dissolved in 25 mL of ethyl acetate
  3. washThe reaction mixture was washed one time each with 10 mL portions of water, 0.1 M NaOH, and saturated aqueous NaCl
  4. dry with materialThe organic layer was dried with MgSO4 and 90 mg of solid
  5. customwas precipitated by the addition of hexanes
  6. customThe material was used without further purification

Sources & evidence

ORD record
ord-8f14615e7300418b91b0ac905a2acb93
Source dataset
uspto-grants-2011_11
Patent number
US08053454B2

Reaction notes

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