Acetonitrile → N4-Acetyl-N1-(1-cyclopropylmethyl-1,2-dihydro-2-oxo-4-pyrimidinyl)sulfanilamide

HRID 328201Notes

Reaction equation

HRID 328201 reaction equation
[CH:1]1([CH2:4][N:5]2[CH:12]=[CH:11][C:9]([NH2:10])=[N:8][C:6]2=[O:7])[CH2:3][CH2:2]1.[C:13]([NH:16][C:17]1[CH:26]=[CH:25][C:20]([S:21](Cl)(=[O:23])=[O:22])=[CH:19][CH:18]=1)(=[O:15])[CH3:14].C(#N)C>C(N(CC)CC)C>[C:13]([NH:16][C:17]1[CH:26]=[CH:25][C:20]([S:21]([NH:10][C:9]2[CH:11]=[CH:12][N:5]([CH2:4][CH:1]3[CH2:2][CH2:3]3)[C:6](=[O:7])[N:8]=2)(=[O:23])=[O:22])=[CH:19][CH:18]=1)(=[O:15])[CH3:14]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 8481N-Acetylsulfanilyl chlorideHCID 214443201-Cyclopropylmethylcytosine

Product 1

HCID 86734625N4-Acetyl-N1-(1-cyclopropylmethyl-1,2-dihydro-2-oxo-4-pyrimidinyl)sulfanilamide

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 495 mg. of 1-cyclopropylmethylcytosine, 702 mg. of N-acetylsulfanilyl chloride, 10 ml. of acetonitrile and 322 mg. of triethylamine was stirred and refluxed for 18 hours. The solvent was evaporated under reduced pressure, and the residue triturated with 10 ml. of water and 3 ml. of 10% aqueous sodium hydroxide. The alkaline solution was decanted from the dark insoluble portion and cleared by filtration. Addition of acetic acid to about pH 5 gave a gummy precipitate which solidified only very slowly. The aqueous solution was decanted and the gum triturated with 2 ml. of hot ethanol, and allowed to settle in an ice bath to obtain after filtration 280 mg. of product, melting at 222°-224°. A sample for analysis was recrystallized from aqueous ethanol; m.p. 225°-226°.

Workup

  1. additionA mixture of 495 mg
  2. temperaturerefluxed for 18 hours
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue triturated with 10 ml
  5. customThe alkaline solution was decanted from the dark insoluble portion
  6. filtrationcleared by filtration
  7. additionAddition of acetic acid to about pH 5
  8. customgave a gummy precipitate which
  9. customThe aqueous solution was decanted
  10. customthe gum triturated with 2 ml
  11. customto settle in an ice bath
  12. customto obtain
  13. filtrationafter filtration 280 mg
  14. customA sample for analysis was recrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-16e5776f1b054d7c9a227ecf743235bf
Source dataset
uspto-grants-1977_04
Patent number
US04016267

Reaction notes

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