Phosgeniminium chloride → HCID 71281789, compound

HRID 1481693Notes

Reaction equation

HRID 1481693 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[OH:12].[Cl-].Cl[C:15](Cl)=[N+:16]([CH3:18])[CH3:17]>C(Cl)Cl>[CH3:15][N:16]([CH3:18])[C:17]1[O:12][C:3]2[CH:4]=[C:5]([C:6]([O:8][CH3:9])=[O:7])[CH:10]=[CH:11][C:2]=2[N:1]=1

Participants

4

Reactant 2

HCID 2723945Phosgeniminium chlorideHCID 7020619Benzoic acid, 4-amino-3-hydroxy-, methyl ester

Product 1

HCID 71281789HCID 71281789, compoundYield 102%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 4-amino-3-hydroxybenzoate (1.63 g, 9.8 mmol) in CH2Cl2 (30 mL) was added N-(dichloromethylene)-N-methylmethanaminium chloride (1.63 g, 10.0 mmol, 1.0 eq). The mixture was heated to reflux for 3 h. The reaction was quenched with H2O then extracted with CH2Cl2 (3×30 mL). Solvent was removed under reduced pressure to afford the title compound (2.2 g, ca. 10.0 mmol) which was used in next step without further purification.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3 h
  3. customThe reaction was quenched with H2O
  4. extractionthen extracted with CH2Cl2 (3×30 mL)
  5. customSolvent was removed under reduced pressure

Sources & evidence

ORD record
ord-c4ae212ec66a4484bc5f6130637f42ab
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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