Phenylacetyl chloride → N-octyl-cis-3-(phenylacetylthio)acrylamide

HRID 1463552

반응식

HRID 1463552 반응식
[CH2:1]([N:9]1[C:13](=[O:14])[CH:12]=[CH:11][S:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:21]1([CH2:27][C:28](Cl)=[O:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>O1CCCC1>[CH2:1]([NH:9][C:13](=[O:14])/[CH:12]=[CH:11]\[S:10][C:28](=[O:29])[CH2:27][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

참가 물질

5

반응물 3

HCID 7679Phenylacetyl chlorideHCID 335282-n-Octyl-4-isothiazolin-3-oneHCID 21226445Aluminium lithium hydride

생성물 1

HCID 86746378N-octyl-cis-3-(phenylacetylthio)acrylamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

To a cooled (-78° C.), stirred solution of 2.0 g (0.0094 mol) of 2-octyl-4-isothiazolin-3-one in 50 ml of anhydrous tetrahydrofuran under nitrogen was added dropwise 2.82 ml (0.0028 mol) of a 1.0M solution of lithium aluminum hydride in tetrahydrofuran over a 20 min. period. After the addition the mixture was stirred at -78° C. for 1 hr. Over a 15 min period 1.24 ml (0.0094 mol) of phenylacetyl chloride was added. After this addition the mixture was allowed to warm to room temperature. After 12 hr the reaction mixture was a white solid suspended in an orange solution. The mixture was filtered and the filtrate was diluted with ethyl acetate and washed once with aqueous saturated sodium bicarbonate solution. The organic layer was set aside and the aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed once with water, with brine, and dried over anhydrous magnesium sulfate. Filtration and removal of solvents gave N-octyl-cis-3 -(phenylacetylthio)acrylamide as an oil which crystallized upon standing to give 3.0 g (96% yield) of a white solid whose NMR is reported in Table 2.

후처리

  1. additionAfter the addition the mixture
  2. additionAfter this addition the mixture
  3. temperatureto warm to room temperature
  4. waitAfter 12 hr the reaction mixture was
  5. filtrationThe mixture was filtered
  6. additionthe filtrate was diluted with ethyl acetate
  7. washwashed once with aqueous saturated sodium bicarbonate solution
  8. extractionthe aqueous layer was extracted three times with ethyl acetate
  9. washThe combined organic layers were washed once with water, with brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. filtrationFiltration and removal of solvents

출처 및 근거

ORD 기록
ord-e022b330793f4c54bcb3526921eba3b4
출처 데이터셋
uspto-grants-1994_04
특허 번호
US05300672

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