Methyl cyanoacetate → Methyl 2-amino-4-(hydroxymethyl)thiophene-3-carboxylate

HRID 601167

反応式

HRID 601167 の反応式
[C:1]([CH2:3][C:4]([O:6][CH3:7])=[O:5])#[N:2].O.O.O.O.O.O.O.O.O.[S-2:17].[Na+].[Na+].C([O:23][CH2:24][C:25]([CH2:27]Cl)=O)(=O)C.C(N(CC)CC)C>CO.O>[NH2:2][C:1]1[S:17][CH:27]=[C:25]([CH2:24][OH:23])[C:3]=1[C:4]([O:6][CH3:7])=[O:5]

参加物

7

反応物 4

HCID 7747Methyl cyanoacetateHCID 8471TriethylamineHCID 384132-Propanone, 1-(acetyloxy)-3-chloro-HCID 73972Sodium sulfide nonahydrate

生成物 1

HCID 15889790Methyl 2-amino-4-(hydroxymethyl)thiophene-3-carboxylate収率 51%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

A solution of methyl cyanoacetate (1.18 mL, 13.28 mmol) and sodium sulfide nonahydrate (3.20 g, 13.28 mmol) in methanol (25 mL) at 0° C. was treated with 1-acetoxy-3-chloroacetone (2.0 g, 13.28 mmol). The cold bath was removed and triethylamine (1.86 mL, 13.28 mmol) was added dropwise. The solution was stirred at room temperature for 20 hours then diluted with water and extracted into ethyl acetate. The organic layer was dried over sodium sulfate, filtered, and the solvent removed under vacuum to provide the titled compound (1.25 g, 51%). MS (DCI/NH3) M/Z 188 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 3.68 (s, 3 H) 4.45 (dd, J=5.52, 1.47 Hz, 2 H) 4.88 (t, J=5.70 Hz, 1 H) 6.12 (s, 1 H) 7.28 (s, 2 H)

後処理

  1. customThe cold bath was removed
  2. extractionextracted into ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. customthe solvent removed under vacuum

出典と根拠

ORDレコード
ord-34d3693602e0460bb323e90f52a7b8b0
出典データセット
uspto-grants-2011_03
特許番号
US07902203B2

関連ノート

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