Benzyl Alcohol → HCID 178508946, compound

HRID 893608Notes

Reaction equation

HRID 893608 reaction equation
[Na].[CH2:2]([OH:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[C:11]1[C:12]2[NH:20][N:19]=[N:18][C:13]=2[N:14]=[C:15]([NH2:17])[N:16]=1>O>[C:3]1([CH2:2][O:9][C:11]2[C:12]3[NH:20][N:19]=[N:18][C:13]=3[N:14]=[C:15]([NH2:17])[N:16]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 5360545Sodium2×HCID 178508438HCID 178508438, compound

Product 1

HCID 178508946HCID 178508946, compoundYield 61.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium metal (3.7 g, 0.162 mol) was added in pieces to benzyl alcohol (117 ml, 1.13 mol) under nitrogen over 20 minutes. The reaction was then heated to 80° for 90 minutes. All of the sodium metal dissolved, and the reaction was left at room temperature for 16 hours. 7-Chloro-1H-1,2,3triazolo[4,5-d]pyrimidin-5-amine (9.23 g. 0.0541 mol) was then added, and the reaction was heated to 60° for 5 hours. The reaction was cooled and left at 5° for 16 hours. Water (500 ml) was added to dissolve the precipitate and then the mixture was extracted with ether (3×200 ml). The pH of the water layer was lowered to 7.0 with concentrated HCl and then to 5.5 with 1N HCl. The precipitate was filtered and dried at room temperature over P2O5 in vacuo to give 8.05 g of desired product.

Workup

  1. temperatureThe reaction was then heated to 80° for 90 minutes
  2. temperaturethe reaction was heated to 60° for 5 hours
  3. temperatureThe reaction was cooled
  4. waitleft at 5° for 16 hours
  5. dissolutionto dissolve the precipitate
  6. extractionthe mixture was extracted with ether (3×200 ml)
  7. filtrationThe precipitate was filtered
  8. dry with materialdried at room temperature over P2O5 in vacuo

Sources & evidence

ORD record
ord-45a9337b7b5b4cff910b4ba78f99b690
Source dataset
uspto-grants-1992_06
Patent number
US05126345

Reaction notes

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