Acetic Acid → 5-(Dimethyl)aminobenzo[b]thiophene

HRID 979564

반응식

HRID 979564 반응식
N[C:2]1[CH:10]=[CH:9][C:5]2[S:6][CH:7]=[CH:8][C:4]=2[CH:3]=1.C=O.[C:13]([BH3-])#[N:14].[Na+].[C:17](O)(=O)C>CC#N.CCOCC>[CH3:17][N:14]([CH3:13])[C:2]1[CH:10]=[CH:9][C:5]2[S:6][CH:7]=[CH:8][C:4]=2[CH:3]=1

참가 물질

7

반응물 4

HCID 176Acetic Acid2회HCID 712FormaldehydeHCID 288032Benzo(b)thiophen-5-amineHCID 5003444Sodium cyanoborohydride

생성물 1

HCID 139229055-(Dimethyl)aminobenzo[b]thiophene수율 88%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6342Acetonitrile용매

실험 절차

To a stirred solution of 5-aminobenzo[b]thiophene (4.55 g, 0.03 mole) in CH3CN (175 ml) was added 37% aqueous formaldehyde (28 ml, 0.035 mole) followed by sodium cyanoborohydride (6.65 g, 0.105 mole). Glacial acetic acid (3.5 ml) was added in small increments over 15 minutes. After 1 hour, another 3.5 ml of acetic acid was added and after another 1 hour, the mixture was poured into ether (700 ml). The ethereal layer was separated, washed with lM KOH (3×) then with saturated NaCl solution, dried over anhydrous Na2SO4, and evaporated to dryness in vacuo. The residual dark oily solid was purified by chromatography on 800 ml of silica gel. Elution with 97 hexane:3 ethyl acetate afforded 4.6 g (88%) of 5-(dimethyl)aminobenzo[b]thiophene as a light yellow solid, m.p. 52°-54° C.

후처리

  1. customThe ethereal layer was separated
  2. washwashed with lM KOH (3×)
  3. dry with materialwith saturated NaCl solution, dried over anhydrous Na2SO4
  4. customevaporated to dryness in vacuo
  5. customThe residual dark oily solid was purified by chromatography on 800 ml of silica gel
  6. washElution with 97 hexane

출처 및 근거

ORD 기록
ord-bd7cf467c2394af8b05fbc7e7b7b1d34
출처 데이터셋
uspto-grants-1987_05
특허 번호
US04668697

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