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

HRID 80218

反応式

HRID 80218 の反応式
[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

参加物

7

反応物 4

HCID 785HydroquinoneHCID 887MethanolHCID 4093Methacrylic AcidHCID 682886-Aminobenzothiazole

生成物 1

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

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 6212Chloroform溶媒

反応条件

温度
100 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-80d35979a62f4716a784efb136d58677
出典データセット
uspto-grants-2014_09
特許番号
USRE045173E1

関連ノート

読み込み中…