Water → HCID 178440955, compound

HRID 1393890Notes

Reaction equation

HRID 1393890 reaction equation
[NH:1]1[CH:8]=[CH:7][C:5]([NH2:6])=[N:4][C:2]1=[O:3].N1C=CC=C[CH:10]=1.ClCCl.[C:18]([C:22]1[CH:30]=[CH:29][CH:28]=[CH:27][C:23]=1C(Cl)=O)([CH3:21])([CH3:20])[CH3:19].[OH2:31]>C(Cl)(Cl)Cl>[CH3:21][C:18]([C:22]1[CH:23]=[CH:27][C:28]([C:10]([NH:6][C:5]2[CH:7]=[CH:8][NH:1][C:2](=[O:3])[N:4]=2)=[O:31])=[CH:29][CH:30]=1)([CH3:19])[CH3:20]

Participants

7

Reactant 5

HCID 962WaterHCID 1049PyridineHCID 6344DichloromethaneHCID 137671862-tert-Butylbenzoyl chlorideHCID 178418229Cytosine

Product 1

HCID 178440955HCID 178440955, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a suspension of cytosine (5.0 grams, 43 mmoles) in a mixture of 1:4 pyridine:dichloromethane (50 ml), tert-butylbenzoyl chloride (Aldrich) (10.6 ml, 56.6 mmoles) was added dropwise. The reaction mixture was stirred at room temperature for four hours and thereafter water (10 ml) and chloroform (40 ml) were added thereto with vigorous stirring. The resulting precipitates were thereafter collected and washed with water. The organic layer in the filtered solution was separated, washed with 1M HCl (30 ml×2) and brine (30 ml) and dried, immediately thereafter, over anhydrous sodium sulfate. The solution was then evaporated to remove about ⅔ of its volume. To the remaining solution (about 20 ml), hexanes (50 ml) were added and the combined precipitates were dried over P2O5, under high vacuum, for eight hours. 11.2 grams (92% yield) of Compound 25 were obtained.

Workup

  1. customThe resulting precipitates
  2. customwere thereafter collected
  3. washwashed with water
  4. customThe organic layer in the filtered solution was separated
  5. washwashed with 1M HCl (30 ml×2) and brine (30 ml)
  6. customdried
  7. customThe solution was then evaporated
  8. customto remove about ⅔ of its volume
  9. additionTo the remaining solution (about 20 ml), hexanes (50 ml) were added
  10. customthe combined precipitates
  11. dry with materialwere dried over P2O5, under high vacuum, for eight hours

Sources & evidence

ORD record
ord-e3524828f51e40659169913f0c59f332
Source dataset
uspto-grants-2008_03
Patent number
US07348148B2

Reaction notes

Loading…