Hydroquinone → 3-(Benzothiazol-6-ylamino)-2-methyl-propionic Acid

HRID 80218

반응식

HRID 80218 반응식
[CH3:1][C:2](=[CH2:6])[C:3]([OH:5])=[O:4].C1(O)C=CC(O)=CC=1.[S:15]1[C:19]2[CH:20]=[C:21]([NH2:24])[CH:22]=[CH:23][C:18]=2[N:17]=[CH:16]1.CO>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl>[S:15]1[C:19]2[CH:20]=[C:21]([NH:24][CH2:6][CH:2]([CH3:1])[C:3]([OH:5])=[O:4])[CH:22]=[CH:23][C:18]=2[N:17]=[CH:16]1

참가 물질

7

반응물 4

HCID 785HydroquinoneHCID 887MethanolHCID 4093Methacrylic AcidHCID 682886-Aminobenzothiazole

생성물 1

HCID 687859923-(Benzothiazol-6-ylamino)-2-methyl-propionic Acid수율 27.4%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 6212Chloroform용매

반응 조건

온도
100 °C

실험 절차

2-Methyl-acrylic acid (0.63 g, 0.00732 mol) and Benzene-1,4-diol (0.029 g, 0.000266 mol) were added to a stirred solution of Benzothiazol-6-ylamine (1 g, 0.00665 mol) in toluene (6 mL) under nitrogen atmosphere. The resulting reaction mass was heated at 70° C. for 72 hours and further at 100° C. for 48 hours. The reaction was monitored by TLC (5% methanol in chloroform). The reaction mixture was cooled to room temperature and partitioned between water and ethyl acetate. The organic layer was washed with brine solution, dried over Na2SO4 and concentrated to afford the crude product. Purification by column chromatography on silica gel (0.75% methanol in chloroform) afforded 0.43 g of the product (26.87% yield).

후처리

  1. customThe resulting reaction mass
  2. temperatureThe reaction mixture was cooled to room temperature
  3. custompartitioned between water and ethyl acetate
  4. washThe organic layer was washed with brine solution
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customto afford the crude product
  8. customPurification by column chromatography on silica gel (0.75% methanol in chloroform)

출처 및 근거

ORD 기록
ord-80d35979a62f4716a784efb136d58677
출처 데이터셋
uspto-grants-2014_09
특허 번호
USRE045173E1

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