Methyl 5-amino-o-anisate → HCID 18464541, compound

HRID 323419

Reaction equation

HRID 323419 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 18464541HCID 18464541, compound

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-thioisocyanatobenzoate: 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-49b52d5f51374e28acdfc541cf98a2de
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Linked notes

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