Water → HCID 19087822, compound

HRID 1464337Notes

Reaction equation

HRID 1464337 reaction equation
[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]2[N:13]=[CH:12]O[C:10](=[O:14])[C:9]=2[CH:15]=1)[CH2:2][CH2:3][CH3:4].[NH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[C:30]2[N:34]([CH2:35][O:36][CH3:37])[N:33]=[N:32][N:31]=2)=[CH:20][CH:19]=1.O>C1(C)C(C)=CC=CC=1>[CH2:1]([C:5]1[CH:15]=[C:9]2[C:8](=[CH:7][CH:6]=1)[N:13]=[CH:12][N:16]([CH2:17][C:18]1[CH:19]=[CH:20][C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[C:30]3[N:34]([CH2:35][O:36][CH3:37])[N:33]=[N:32][N:31]=3)=[CH:22][CH:23]=1)[C:10]2=[O:14])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 19087812HCID 19087812, compoundHCID 19087842HCID 19087842, compound

Product 1

HCID 19087822HCID 19087822, compoundYield 43.6%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 6-n-butyl-4H-3,1-benzoxazin-4-one (1.4 g, 6.89 mmol) and 5-(4'-aminomethylbiphenyl-2-yl)-N-methoxymethyltetrazole (2.85 g, ca. 9.65 mmol) in xylene (50 ml) was heated under reflux for 8 hours while water was removed by a Dean-Stark trap. After cooling, the reaction mixture was concentrated in vacuo. The resulting residue was purified by flash column chromatography on silica gel. The column was eluted with chloroform-ethyl acetate (1% to 10%) to give 1.44 g (43.6%) of the title compound as a colorless crystal.

Workup

  1. temperaturewas heated
  2. customwas removed by a Dean-Stark trap
  3. temperatureAfter cooling
  4. concentrationthe reaction mixture was concentrated in vacuo
  5. customThe resulting residue was purified by flash column chromatography on silica gel
  6. washThe column was eluted with chloroform-ethyl acetate (1% to 10%)

Sources & evidence

ORD record
ord-afc09ac0230e4eb6a8ab34708ef88060
Source dataset
uspto-grants-1994_04
Patent number
US05304565

Reaction notes

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