m-Chloroperbenzoic acid → N-[[(1-Methylethyl)amino]carbonyl]-4-(methylsulfinyl)-2-amino-5-pyrimidinesulfonamide

HRID 1721868ノート

反応式

HRID 1721868 の反応式
[NH2:1][C:2]1[N:7]=[C:6]([S:8][CH3:9])[C:5]([S:10]([NH:13][C:14]([NH:16][CH:17]([CH3:19])[CH3:18])=[O:15])(=[O:12])=[O:11])=[CH:4][N:3]=1.[Na].C(C1C=CC=CC=1)(=[O:28])C1C=CC=CC=1.ClC1C=CC=C(C(OO)=O)C=1>C1COCC1>[CH3:18][CH:17]([NH:16][C:14]([NH:13][S:10]([C:5]1[C:6]([S:8]([CH3:9])=[O:28])=[N:7][C:2]([NH2:1])=[N:3][CH:4]=1)(=[O:12])=[O:11])=[O:15])[CH3:19]

参加物

5

反応物 3

HCID 70297m-Chloroperbenzoic acidHCID 198603812-Amino-N-[[(1-methylethyl)amino]carbonyl]-4-(methylthio)-5-pyrimidinesulfonamideHCID 66591377Sodium benzophenone

生成物 1

HCID 19860380N-[[(1-Methylethyl)amino]carbonyl]-4-(methylsulfinyl)-2-amino-5-pyrimidinesulfonamide収率 84%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

2-Amino-N-[[(1-methylethyl)amino]carbonyl]-4-(methylthio)-5-pyrimidinesulfonamide (3.0 g, 9.84 mmol) was dissolved in dry (freshly distilled from sodium/benzophenone) THF (60 mL) and m-chloroperbenzoic acid (MCPBA) (2.55 g, 11.81 mmol, 80% 1.2 eq) was added as a solid. The reaction turned yellow and a white solid precipitated out of solution. After 30 minutes the reaction was diluted with ethyl ether (60 mL) and the white solid was filtered, washed with THF, then with ether three times and air dried for 2 hours, to yield 2.64 g (8.22 mmol, 84%) of product, m.p. 140° C.(dec.). The product was unstable to heat but could be stored under nitrogen in the freezer for weeks.

後処理

  1. customin dry (
  2. additionwas added as a solid
  3. customa white solid precipitated out of solution
  4. additionAfter 30 minutes the reaction was diluted with ethyl ether (60 mL)
  5. filtrationthe white solid was filtered
  6. washwashed with THF
  7. dry with materialwith ether three times and air dried for 2 hours

出典と根拠

ORDレコード
ord-750466eeec1446298c08f1d0fcea07c9
出典データセット
uspto-grants-1989_08
特許番号
US04853389

反応ノート

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