Ethyl 2-aminobenzoate → HCID 19169956, compound

HRID 726847Notes

Reaction equation

HRID 726847 reaction equation
[CH2:1]([N:4]=[C:5]=[O:6])[CH2:2][CH3:3].[C:7]([O:16][CH2:17][CH3:18])(=[O:15])[C:8]1[C:9](=[CH:11][CH:12]=[CH:13][CH:14]=1)[NH2:10].C(N(CC)CC)C.C(N1C(=O)C2C(=CC=CC=2)NC1=O)CC>C1(C)C(C)=CC=CC=1>[CH2:1]([NH:4][C:5]([NH:10][C:9]1[C:8](=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:7]([O:16][CH2:17][CH3:18])=[O:15])=[O:6])[CH2:2][CH3:3]

Participants

6

Reactant 4

HCID 6877Ethyl 2-aminobenzoateHCID 8471TriethylamineHCID 61033Propyl isocyanateHCID 43446443-Propyl-1H-quinazoline-2,4-dione

Product 1

HCID 19169956HCID 19169956, compoundYield 66.9%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Conditions

Temperature
110 °C

Procedure

A solution of propyl isocyanate (34.0 g, 0.40 mol) in xylene (100 ml) is metered, at room temperature, into a solution of ethyl anthranilate (66.1 g, 0.40 mol) in xylene (200 ml). After the addition has ended, the batch is stirred at 110° C. for 2 hours. Triethylamine (5.6 ml, 4.08 g, 0,040 mol) is added. Stirring is continued at 90° C. for a further 2 hours. The desired cyclization product 3-(propyl)-2,4(1H,3H)-quinazolinedione cannot be detected in the reaction solution by thin-layer chromatography. After cooling, the precipitate is filtered off with suction, washed with 3×25 ml of xylene and dried. 67.0 g of ethyl N-(propylcarbamoyl)anthranilate (yield: 66.9% of theory) of melting point 98° to 99° C. are obtained.

Workup

  1. additionAfter the addition
  2. stirringStirring
  3. waitis continued at 90° C. for a further 2 hours
  4. temperatureAfter cooling
  5. filtrationthe precipitate is filtered off with suction
  6. washwashed with 3×25 ml of xylene
  7. customdried

Sources & evidence

ORD record
ord-e18215816e944b088e14ad34e9a4c375
Source dataset
uspto-grants-1998_01
Patent number
US05710319

Reaction notes

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