Thiourea → N-(4-(2-aminothiazol-4-yl)-3,5-dimethylphenyl)acetamide

HRID 1843745ノート

反応式

HRID 1843745 の反応式
Br[CH2:2][C:3]([C:5]1[C:10]([CH3:11])=[CH:9][C:8]([NH:12][C:13](=[O:15])[CH3:14])=[CH:7][C:6]=1[CH3:16])=O.[NH2:17][C:18]([NH2:20])=[S:19]>CCO>[NH2:20][C:18]1[S:19][CH:2]=[C:3]([C:5]2[C:10]([CH3:11])=[CH:9][C:8]([NH:12][C:13](=[O:15])[CH3:14])=[CH:7][C:6]=2[CH3:16])[N:17]=1

参加物

4

反応物 2

HCID 2723790ThioureaHCID 18788447N-(4-(2-bromoacetyl)-3,5-dimethylphenyl)acetamide

生成物 1

HCID 58442517N-(4-(2-aminothiazol-4-yl)-3,5-dimethylphenyl)acetamide収率 86.5%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of N-(4-(2-bromoacetyl)-3,5-dimethylphenyl)acetamide (7.34 g, 25.8 mmol) and thiourea (1.97 g, 25.9 mmol) in 95% EtOH (36.9 mL) was heated at reflux for 120 min. The solution was concentrated and added with water (100 mL) and saturated aqueous Na2CO3 (5.0 mL). The resultant precipitate was filtered and recrystallized in toluene (50 mL). The solids were filtered and dried under vacuum to give N-(4-(2-aminothiazol-4-yl)-3,5-dimethylphenyl)acetamide (5.83 g) as yellow solids in 86% yield: 1H NMR (500 MHz, DMSO-d6) δ 9.80 (s, 1 H), 7.26 (s, 2 H), 6.90 (bs, 2 H), 6.30 (s, 1 H), 2.06 (s, 6 H), 2.02 (s, 3 H).

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 120 min
  3. concentrationThe solution was concentrated
  4. additionadded with water (100 mL) and saturated aqueous Na2CO3 (5.0 mL)
  5. filtrationThe resultant precipitate was filtered
  6. customrecrystallized in toluene (50 mL)
  7. filtrationThe solids were filtered
  8. customdried under vacuum

出典と根拠

ORDレコード
ord-1f36238db0dd4db6b28b06b47acf54ca
出典データセット
uspto-grants-2015_02
特許番号
US08946268B2

反応ノート

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