Dimethylamine → 4-[(N,N-Dimethylamino)carbonyl]-2-thiophenecarboxaldehyde

HRID 486134노트

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HRID 486134 반응식
[CH:1]([C:3]1[S:4][CH:5]=[C:6]([C:8]([OH:10])=O)[CH:7]=1)=[O:2].[C:11](N1C=CN=C1)([N:13]1C=CN=[CH:14]1)=O.CNC>O1CCCC1>[CH3:11][N:13]([C:8]([C:6]1[CH:7]=[C:3]([CH:1]=[O:2])[S:4][CH:5]=1)=[O:10])[CH3:14]

참가 물질

5

반응물 3

HCID 674DimethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 8188835-Formylthiophene-3-carboxylic acid

생성물 1

HCID 150073524-[(N,N-Dimethylamino)carbonyl]-2-thiophenecarboxaldehyde수율 79%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 2-formyl-4-thiophenecarboxylic acid (prepared according to Gronowitz, S., et al., Arkiv. for Kemi. 21:265 (1963)) (1.24 g, 7.94 mmoles) in 50 ml of tetrahydrofuran was added 1,1'-carbonyldiimidazole (1.80 g, 11.10 mmoles) the solution stirred under dry argon for 11/2 hours and treated with excess gaseous dimethylamine. The solution was concentrated in vacuo to an oil which was dissolved in ethyl acetate (60 ml) and extracted with 1N hydrochloric acid (1×30 ml) followed by 5% sodium bicarbonate (1×30 ml). Each of the aqueous extracts was backwashed with ethyl acetate (2×50 ml) and the combined organic layers were dried (magnesium sulfate). Concentration in vacuo furnished a tan solid (1.15 g, 79%). EIMS (m/z): 183 (M+, 31%), 155 (M+ -CO, 38%), 139 (M+ -(CH3)2N, base) and 111 (M+ -(CH3) 2 NCO, 25%); 1HNMR (DMSO-d6) delta, 9.89 (1H, d, J=1.4Hz), 7.89 (1H, dd, J=1.5, 1.4Hz), 7.86 (1H, d, J=1.5Hz), 3.08 (6H, s). This material was used directly without further purification.

후처리

  1. concentrationThe solution was concentrated in vacuo to an oil which
  2. dissolutionwas dissolved in ethyl acetate (60 ml)
  3. extractionextracted with 1N hydrochloric acid (1×30 ml)
  4. dry with materialthe combined organic layers were dried (magnesium sulfate)
  5. concentrationConcentration in vacuo

출처 및 근거

ORD 기록
ord-5605ef4851114992a4a619a6c6e6167c
출처 데이터셋
uspto-grants-1994_03
특허 번호
US05290802

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