Benzyl chloroformate → HCID 178522340, compound

HRID 50077Notes

Reaction equation

HRID 50077 reaction equation
[CH2:1]([O:8][C:9](Cl)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:12]1[CH:19]=[CH:18][C:16]([NH2:17])=[N:15][C:13]1=[O:14]>N1C=CC=CC=1>[CH2:1]([O:8][C:9]([NH:17][C:16]1[CH:18]=[CH:19][NH:12][C:13](=[O:14])[N:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 10387Benzyl chloroformateHCID 178418229Cytosine

Product 1

HCID 178522340HCID 178522340, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

Over a period of about 1 h, benzyloxycarbonyl chloride (52 mL, 0.36 mol) was added dropwise to a suspension of cytosine (8, 20 g, 0.18 mol) in dry pyridine (1000 mL) at 0° C. under nitrogen in oven-dried equipment. The solution then was stirred overnight, after which the pyridine suspension was evaporated to dryness, in vacuo. Water (200 mL) and 4 N hydrochloric acid were added to reach pH ˜1. The resulting white precipitate was filtered off, washed with water and partially dried by air suction. The moist precipitate was refluxed with absolute ethanol (500 mL) for 10 minutes, cooled to 0° C., filtered, washed thoroughly with ether, and dried, in vacuo. Yield 24.7 g (54%). M.p.>250° C. Anal. for C12H11N3O3. Found(calc.); C: 58.59(58.77); H: 4.55(4.52); N: 17.17(17.13). No NMR spectra were recorded since it was not possible to get the product dissolved.

Workup

  1. customafter which the pyridine suspension was evaporated to dryness, in vacuo
  2. additionWater (200 mL) and 4 N hydrochloric acid were added
  3. filtrationThe resulting white precipitate was filtered off
  4. washwashed with water
  5. custompartially dried by air suction
  6. temperatureThe moist precipitate was refluxed with absolute ethanol (500 mL) for 10 minutes
  7. filtrationfiltered
  8. washwashed thoroughly with ether
  9. customdried, in vacuo
  10. customto get the product
  11. dissolutiondissolved

Sources & evidence

ORD record
ord-e66ba660a3964be78f55f0e2fd997c4c
Source dataset
uspto-grants-2004_03
Patent number
US06710164B1

Reaction notes

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