Methyl 2-amino-5-(propan-2-yl)-1,3-thiazole-4-carboxylate → Methyl 5-isopropylthiazole-4-carboxylate

HRID 244667ノート

反応式

HRID 244667 の反応式
N[C:2]1[S:3][C:4]([CH:11]([CH3:13])[CH3:12])=[C:5]([C:7]([O:9][CH3:10])=[O:8])[N:6]=1.N([O-])=O.[Na+]>OP=O>[CH3:13][CH:11]([C:4]1[S:3][CH:2]=[N:6][C:5]=1[C:7]([O:9][CH3:10])=[O:8])[CH3:12]

参加物

4

反応物 2

HCID 737584Methyl 2-amino-5-(propan-2-yl)-1,3-thiazole-4-carboxylateHCID 23668193Sodium Nitrite

生成物 1

HCID 13015587Methyl 5-isopropylthiazole-4-carboxylate収率 95.5%

試薬・触媒・溶媒 1

HCID 22497phosphenous acid溶媒

反応条件

温度
0 °C

実験手順

To a solution of methyl 2-amino-5-(1-methylethyl)-1,3-thiazole-4-carboxylate (2.15 g) (available from ABCR) in 30% hypophosphorus acid (53 ml) at −5° C. was added, slowly beneath the surface, maintaining the temperature between −5 and 0° C., sodium nitrite (1.6 g) and the mixture was stirred for a further 1 h at 0° C. The cooling bath was removed for 2 h, then replaced while a cool solution of sodium hydroxide (8.5 g) in water (100 ml) added slowly. The solution was neutralised by the addition of solid sodium hydrogencarbonate and extracted with diethyl ether (50 ml), then dried over sodium sulphate. The mixture was evaporated and purified by chromatography on silica gel eluting with a gradient of ethyl acetate in cyclohexane to give the title compound (1.9 g) as a yellow oil.

後処理

  1. customThe cooling bath was removed for 2 h
  2. additionadded slowly
  3. additionThe solution was neutralised by the addition of solid sodium hydrogencarbonate
  4. extractionextracted with diethyl ether (50 ml)
  5. dry with materialdried over sodium sulphate
  6. customThe mixture was evaporated
  7. custompurified by chromatography on silica gel eluting with a gradient of ethyl acetate in cyclohexane

出典と根拠

ORDレコード
ord-d6570c87c80f48d29033f456e686f49e
出典データセット
uspto-grants-2014_02
特許番号
US08658635B2

反応ノート

読み込み中…