Methyl 2-Amino-4-bromobenzoate → HCID 178497427, compound

HRID 1619366Notes

Reaction equation

HRID 1619366 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([Br:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Cl-].[Cl:14][C:15]1[NH2+:16][S:17][S:18][C:19]=1Cl>C(Cl)Cl>[Br:12][C:10]1[CH:9]=[CH:8][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2](/[N:1]=[C:19]2\[C:15]([Cl:14])=[N:16][S:17][S:18]\2)[CH:11]=1

Participants

4

Reactant 2

HCID 17871390Methyl 2-Amino-4-bromobenzoateHCID 227235124,5-Dichloro-1,2,3-dithiazolium chloride

Product 1

HCID 178497427HCID 178497427, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of methyl 2-amino-4-bromobenzoate (1.0 g, 4.34 mmol, 1 eq) and 4,5-dichloro-1,2,3-dithiazolium chloride (2.0 g, 9.6 mmol, 2.2 eq) in DCM (20 mL) was stirred at rt under N2 for 5 days. The reaction mixture was quenched with water and filtered. The filtrate was extracted with ethyl acetate (3×100 mL). The combined organic layers were dried over Na2SO4. After filtration and concentration, the residue was purified by silica gel chromatography to give the desired product. MS (ESI): 365, 367 (MH+).

Workup

  1. customThe reaction mixture was quenched with water
  2. filtrationfiltered
  3. extractionThe filtrate was extracted with ethyl acetate (3×100 mL)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationAfter filtration and concentration
  6. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-36d63b08316f4085b8d69fb891be2f54
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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