Triethylamine → HCID 6458126, compound

HRID 726846Notes

Reaction equation

HRID 726846 reaction equation
[CH2:1]([N:8]=[C:9]=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:11]([O:20][CH3:21])(=[O:19])[C:12]1[C:13](=[CH:15][CH:16]=[CH:17][CH:18]=1)[NH2:14].C(N(CC)CC)C.C(N1C(=O)C2C(=CC=CC=2)NC1=O)C1C=CC=CC=1>C1(C)C(C)=CC=CC=1>[CH2:1]([NH:8][C:9]([NH:14][C:13]1[C:12](=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:11]([O:20][CH3:21])=[O:19])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8635Methyl AnthranilateHCID 76639Benzyl isocyanateHCID 710807HCID 710807, compound

Product 1

HCID 6458126HCID 6458126, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Conditions

Temperature
110 °C

Procedure

A solution of benzyl isocyanate (13.3 g, 0.10 mol) in xylene (40 ml) is metered, at room temperature, into a solution of methyl anthranilate (15.1 g, 0.10 mol) in xylene (80 ml). After the addition has ended, the batch is stirred at 110° C. for 2 hours. Triethylamine (1.4 ml, 1.01 g, 0,010 mol) is added. The mixture is stirred at 90° C. for a further 2 hours. The desired cyclization product 3-(benzyl)-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. 23.1 g of methyl N-(benzylcarbamoyl)anthranilate (yield: 81.3% of theory) of melting point 140° to 141° C. (lit. 139° to 140° C.) are obtained.

Workup

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

Sources & evidence

ORD record
ord-9c8c94b1bf6d4f5686896b0cc8c6e1fe
Source dataset
uspto-grants-1998_01
Patent number
US05710319

Reaction notes

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