Dichloromethane → Sc-36741

HRID 1607518Notes

Reaction equation

HRID 1607518 reaction equation
C([O:3][CH2:4][CH2:5][C:6]1[C:7]2[N:8]([N:19]=[CH:20][N:21]=2)[C:9]([NH2:18])=[N:10][C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)C.B(Cl)(Cl)Cl.ClCCl>O>[OH:3][CH2:4][CH2:5][C:6]1[C:7]2[N:8]([N:19]=[CH:20][N:21]=2)[C:9]([NH2:18])=[N:10][C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 25135Boron TrichlorideHCID 55784Bemitradine

Product 1

HCID 175635Sc-36741

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 28 g (0.1 mmole) of 8-(2-ethoxyethyl)-7-phenyl-1,2,4-triazolo[2,3-c]pyrimidine-5-amine (which is prepared by methods described in U.S. Pat. No. 4,405,780, the entire disclosure of which is incorporated herein by reference) was added 200 mL of 1N boron trichloride and dichloromethane. The mixture was then stirred at room temperature overnight, after which 500 mL of water was added. After three hours, the resultant precipitate was collected by filtration. The agueous phase of the filter wa separated and neutralized with agueous sodium carbonate, giving a second precipitate. The combined solids were purified by column chromatography, giving the titled compound, m.p. 194°-195°.

Workup

  1. waitAfter three hours
  2. filtrationthe resultant precipitate was collected by filtration
  3. customThe agueous phase of the filter wa separated
  4. customgiving a second precipitate
  5. customThe combined solids were purified by column chromatography

Sources & evidence

ORD record
ord-6126fd50220147fcbe3c460f3dc56d64
Source dataset
uspto-grants-1989_09
Patent number
US04866063

Reaction notes

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