Dimethylformamide → HCID 22466704, compound

HRID 1935080Notes

Reaction equation

HRID 1935080 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([O:12][CH2:13][CH3:14])[C:9]([O:15][CH2:16][CH3:17])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].P(Cl)(Cl)(Cl)=O.[OH-].[Na+].[CH3:25][N:26]([CH:28]=O)[CH3:27]>C(Cl)Cl>[CH3:25][N:26]([CH:28]=[N:1][C:2]1[CH:11]=[C:10]([O:12][CH2:13][CH3:14])[C:9]([O:15][CH2:16][CH3:17])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5])[CH3:27]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 3516698methyl 2-amino-4,5-diethoxybenzoate

Product 1

HCID 22466704HCID 22466704, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
55 °C

Procedure

To a stirred solution of methyl 2-amino-4,5-diethoxybenzoate (4.79 g, 20 mmol) in 20 ml of DMF at 0° C. was added phosphorous oxychloride (2.24 ml, 24 mmol) during 15 m. The mixture was warmed to 55° C. and stirred for 45 m. The resulting solution was diluted with methylene chloride, cooled to 0° C., and treated with 80 ml of precooled N/1 sodium hydroxide during 5 m. The organic layer was separated and washed at 0° C. with with water. The solution was dried and concentrated to give an amber oil; NMR (CDCl3) δ 3.00(s, Me2N).

Workup

  1. temperaturecooled to 0° C.
  2. customThe organic layer was separated
  3. washwashed at 0° C. with with water
  4. customThe solution was dried
  5. concentrationconcentrated
  6. customto give an amber oil

Sources & evidence

ORD record
ord-5a08d7828e144e2e800992a5a2c2b250
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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