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

HRID 2383904Notes

Reaction equation

[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

Participants

Conditions

Temperature: 100 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-b54d83c782fd4fb889acb1af7310bbcc
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263635B2

Reaction notes

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