Triethylamine → HCID 20208408, compound

HRID 542491Notes

Reaction equation

HRID 542491 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([NH2:11])[C:7]=1[C:8]([OH:10])=[O:9].C(N(CC)CC)C.[N:19]1([C:28](Cl)=O)[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[N:21]=[N:20]1>C1(C)C=CC=CC=1>[N:19]1([C:28]2[O:9][C:8](=[O:10])[C:7]3[C:2]([CH3:1])=[CH:3][CH:4]=[CH:5][C:6]=3[N:11]=2)[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[N:21]=[N:20]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1512106-Methylanthranilic acidHCID 3694189Benzotriazole-1-carbonyl chloride

Product 1

HCID 20208408HCID 20208408, compoundYield 22.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 960 mg of 6-methyl anthranilic acid in 30 ml of dry toluene containing 1.77 ml of dry triethylamine, which had been stirred for 30 minutes, was added to a solution of 2.1 gm of 1-benzotriazole carboxylic acid chloride in 30 ml toluene over a period of 30 minutes, and stirred for 12 hours. The resulting precipitate was filtered. The filtrate was reduced to one-half of its initial volume, and the resulting solids isolated by filtration. The combined residues were washed with water, dried under high vacuum and recrystallized from chloroform, giving 400 mg of 2-(1-benzotriazolyl)-5-methyl-4H-3,1-benzoxazin-4-one, m.p. 214°-215° C. (decomp.).

Workup

  1. filtrationThe resulting precipitate was filtered
  2. customthe resulting solids isolated by filtration
  3. washThe combined residues were washed with water
  4. customdried under high vacuum
  5. customrecrystallized from chloroform

Sources & evidence

ORD record
ord-ffcaa2414bf349d1afb21f360384c55e
Source dataset
uspto-grants-1987_04
Patent number
US04657893

Reaction notes

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