Ethyl 2-aminobenzoate → HCID 57974171, compound

HRID 1864061Notes

Reaction equation

HRID 1864061 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([Cl:9])=[CH:4][N:3]=1.[NH2:10][C:11]1[CH:21]=[CH:20][CH:19]=[CH:18][C:12]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14].C(N(C(C)C)CC)(C)C>C(O)C>[Cl:1][C:2]1[N:7]=[C:6]([NH:10][C:11]2[CH:21]=[CH:20][CH:19]=[CH:18][C:12]=2[C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:5]([Cl:9])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 6877Ethyl 2-aminobenzoateHCID 81531DiisopropylethylamineHCID 2372592,4,5-Trichloropyrimidine

Product 1

HCID 57974171HCID 57974171, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A round-bottomed flask was charged with 2,4,5-trichloropyrimidine (5 mL, 43.6 mmol), ethyl 2-aminobenzoate (7.6 g, 46.0 mmol), di-isopropyl-ethylamine (8.3 mL, 48.0 mmol) and ethanol (60 mL). The flask was fitted with a reflux condenser and the reaction was heated to reflux and stirred for 18 h. A white solid appeared in the reaction mixture. The reaction was cooled to room temperature, and the solid was filtered off and washed with ethanol (100 mL), ethanol/hexane (1:1, 200 mL) and hexane (200 mL) to afford the product (10.2 g, 32.7 mmol, 75% yield) as a white solid. MS: M(C13H11Cl2N3O2)=312.15, (M+H)+=312.0 and 314.0.

Workup

  1. customThe flask was fitted with a reflux condenser
  2. temperaturethe reaction was heated
  3. temperatureto reflux
  4. filtrationthe solid was filtered off
  5. washwashed with ethanol (100 mL), ethanol/hexane (1:1, 200 mL) and hexane (200 mL)

Sources & evidence

ORD record
ord-2d3fa4c24dd54bd8b6c01542b6b74943
Source dataset
uspto-grants-2009_12
Patent number
US07625903B2

Reaction notes

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