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

HRID 328201ノート

反応式

HRID 328201 の反応式
[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]

参加物

5

反応物 3

HCID 6342AcetonitrileHCID 8481N-Acetylsulfanilyl chlorideHCID 214443201-Cyclopropylmethylcytosine

生成物 1

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

試薬・触媒・溶媒 1

HCID 8471Triethylamine溶媒

実験手順

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°.

後処理

  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

出典と根拠

ORDレコード
ord-16e5776f1b054d7c9a227ecf743235bf
出典データセット
uspto-grants-1977_04
特許番号
US04016267

反応ノート

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