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

HRID 637162

Reaction equation

HRID 637162 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-4ac3dee6d5d94c8aa6b1ae1554ac0251
Source dataset
uspto-grants-2001_02
Patent number
US06194406B1

Linked notes

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