Methyl 5-amino-o-anisate → Methyl5-isothiocyanato-2-methoxybenzoate

HRID 2230740

Reaction equation

HRID 2230740 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([NH2:10])[CH:7]=[CH:6][C:5]=1[O:11][CH3:12].C1C=C(O[C:21](OC2N=CC=CC=2)=[S:22])N=CC=1>ClCCl>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([N:10]=[C:21]=[S:22])[CH:7]=[CH:6][C:5]=1[O:11][CH3:12]

Participants

4

Reactant 2

HCID 89843Methyl 5-amino-o-anisateHCID 719784O,O-Dipyridin-2-yl carbonothioate

Product 1

HCID 18464541Methyl5-isothiocyanato-2-methoxybenzoateYield 72.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Treat a solution of 5-amino-2-methoxy-benzoic acid methyl ester (7.70 g, 42.5 mmol) and dichloromethane (50 mL) portionwise with a solution of di-2-pyridyl thionocarbonate (10.0 g, 43.1 mmol; Aldrich Chemical Company) and dichloromethane (70 mL) at room temperature under an argon atmosphere. After 3.5 hours, concentrate in vacuo and purify the residue by flash chromatography (silica gel, 5.5×17.8 cm) eluting with dichloromethane. Combine the appropriate fractions and concentrate to afford 5-isothiocyanato-2-methoxy-benzoic acid methyl ester (6.9 g).

Workup

  1. concentrationconcentrate in vacuo
  2. custompurify the residue by flash chromatography (silica gel, 5.5×17.8 cm)
  3. washeluting with dichloromethane
  4. concentrationconcentrate

Sources & evidence

ORD record
ord-746ee47147d54790a5d65f29c0231d49
Source dataset
uspto-grants-2002_07
Patent number
US06423704B1

Linked notes

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