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

HRID 1465609ノート

反応式

HRID 1465609 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 86.4%

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, 25.9 g 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 (s, 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-647ea89b6969400d8365a4a1ed32899b
出典データセット
uspto-grants-2015_04
特許番号
US08999983B2

反応ノート

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