Dichloromethane → (trans)-N-Methoxy-N-methyl-3-(2,3-Dihydrobenzodioxin-5-yl)propenamide

HRID 1107556노트

반응식

HRID 1107556 반응식
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10](/[CH:11]=[CH:12]/[C:13]([OH:15])=O)[C:5]=2[O:4][CH2:3][CH2:2]1.S(Cl)(Cl)=O.C(Cl)Cl.Cl.[CH3:24][NH:25][O:26][CH3:27]>C(OCC)(=O)C.C([O-])([O-])=O.[Na+].[Na+].O>[CH3:27][O:26][N:25]([CH3:24])[C:13](=[O:15])/[CH:12]=[CH:11]/[C:10]1[C:5]2[O:4][CH2:3][CH2:2][O:1][C:6]=2[CH:7]=[CH:8][CH:9]=1

참가 물질

8

반응물 4

HCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 5343159(E)-3-(2,3-dihydrobenzo[b][1,4]dioxin-5-yl)acrylic acid

생성물 1

HCID 18787407(trans)-N-Methoxy-N-methyl-3-(2,3-Dihydrobenzodioxin-5-yl)propenamide

시약·촉매·용매 3

HCID 962Water용매HCID 8857Ethyl Acetate용매2회HCID 10340Sodium Carbonate용매

실험 절차

A mixture of (trans)-3-(2,3-dihydrobenzodioxin-5-yl)propenoic acid (9.83 g, 47.7 mmol), thionyl chloride (20 mL), and CH2Cl2 (75 mL) was heated to reflux for 1 hr, and then concentrated in vacuo to give a yellow-green solid. This material was dissolved in ethyl acetate (75 mL), and a solution of N,O-dimethylhydroxylamine hydrochloride (9.5 g) in saturated Na2CO3 (100 mL) was added with stirring. The mixture was stirred for 90 min and then diluted with water and ethyl acetate. The ethyl acetate layer was separated and washed twice with water and twice with saturated Na2CO3. The ethyl acetate layer was concentrated in vacuo to give a brown oil. This crude product was chromatographed on silica gel using 1:1 ethyl acetate/methylene chloride as the eluent to give a clear oil that crystallized upon standing (11.1 g, 93.1%)

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 1 hr
  3. concentrationconcentrated in vacuo
  4. customto give a yellow-green solid
  5. stirringThe mixture was stirred for 90 min
  6. customThe ethyl acetate layer was separated
  7. washwashed twice with water and twice with saturated Na2CO3
  8. concentrationThe ethyl acetate layer was concentrated in vacuo
  9. customto give a brown oil
  10. customThis crude product was chromatographed on silica gel using 1:1 ethyl acetate/methylene chloride as the eluent
  11. customto give a clear oil that
  12. customcrystallized

출처 및 근거

ORD 기록
ord-2d90bba683db4b44a086a1600c97de6e
출처 데이터셋
uspto-grants-2000_05
특허 번호
US06060506

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