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

HRID 601167

반응식

HRID 601167 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-34d3693602e0460bb323e90f52a7b8b0
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902203B2

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