Triethylamine → HCID 135817487, compound

HRID 2086098Notes

Reaction equation

HRID 2086098 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:9][C:10]2[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=2[C:12](=O)[N:13]=1.Cl.[C:20]([C:22]1[CH:30]=[CH:29][C:25]([CH2:26][NH:27][NH2:28])=[CH:24][CH:23]=1)#[N:21].C(N(CC)CC)C>C(O)C>[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]=[C:12]([C:11]2[CH:15]=[CH:16][CH:17]=[CH:18][C:10]=2[OH:9])[N:27]([CH2:26][C:25]2[CH:29]=[CH:30][C:22]([C:20]#[N:21])=[CH:23][CH:24]=2)[N:28]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 227280904-(hydrazinylmethyl)benzonitrile hydrochlorideHCID 1356857232-(2-Hydroxyphenyl)-4H-1,3-benzoxazin-4-one

Product 1

HCID 135817487HCID 135817487, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5.0 g of 2-(2-hydroxyphenyl)benz[e][1,3]oxazin-4-one, 3.9 g of 4-cyanobenzylhydrazine hydrochloride and 6 ml of triethylamine are boiled under reflux for 3 h in 50 ml of ethanol. The mixture is cooled, poured onto water and extracted with ethyl acetate. The combined organic phases are dried over sodium sulfate and concentrated on a rotary evaporator. The residue is crystallized from ethanol/water. After drying, 4-[3,5-bis(2-hydroxyphenyl)-[1,2,4]triazol-1-ylmethyl]benzonitrile remains as colorless crystals of m.p. 147-149° C.

Workup

  1. temperatureThe mixture is cooled
  2. additionpoured onto water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic phases are dried over sodium sulfate
  5. concentrationconcentrated on a rotary evaporator
  6. customThe residue is crystallized from ethanol/water
  7. customAfter drying

Sources & evidence

ORD record
ord-1b94c62cf4d34b4bb3adfe66a1aea42d
Source dataset
uspto-grants-2004_04
Patent number
US06723742B2

Reaction notes

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