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

HRID 2230629Notes

Reaction equation

HRID 2230629 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].C1C=C(O[C:21](OC2N=CC=CC=2)=[S:22])N=CC=1>ClCCl>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([N:13]=[C:21]=[S:22])=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]

Participants

4

Reactant 2

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

Product 1

HCID 18464541Methyl5-isothiocyanato-2-methoxybenzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

According to the method of Tet. Let., 26, 1661 (1985), combine methyl 2-methoxy-5-aminobenzoate (0.5 g, 2.76 mmol) and di-2-pyridyl thionocarbonate (0.64 g, 2.76 mmol) in dichloromethane (10 mL). After 30 minutes, dilute the reaction mixture with dichloromethane and extract five times with water. Dry the organic layer over Na2SO4, filter, and concentrate in vacuo to give methyl 2-methoxy-5-isothiocyanatobenzoate: Rf=0.51 (silica gel, dichloromethane).

Workup

  1. extractionextract five times with water
  2. dry with materialDry the organic layer over Na2SO4
  3. filtrationfilter
  4. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-0b6053ef971143bcb0bef53115d2f0a5
Source dataset
uspto-grants-2002_07
Patent number
US06423704B1

Reaction notes

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