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

HRID 486134ノート

反応式

HRID 486134 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5605ef4851114992a4a619a6c6e6167c
出典データセット
uspto-grants-1994_03
特許番号
US05290802

反応ノート

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