2-Amino-4,5,6,7-tetrahydrobenzothiazole → 2-methylsulfanyl-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-1,4a-diaza-fluorene-3-carboxylic acid

HRID 68936

Reaction equation

[S:1]1[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:4]=2[N:3]=[C:2]1[NH2:10].[CH2:11]([S:13][C:14](SCC)=[C:15]1[C:20](=O)[O:19]C(C)(C)[O:17][C:16]1=[O:24])C>C(O)C>[CH3:11][S:13][C:14]1[N:10]=[C:2]2[N:3]([C:20](=[O:19])[C:15]=1[C:16]([OH:24])=[O:17])[C:4]1[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=1[S:1]2

Participants

Conditions

Temperature: 87.5 °C

Procedure

The suspension of 4,5,6,7-tetrahydro-benzothiazol-2-yl-amine (8 gm, 0.0519 mol) and 5-(bis-ethylsulfanyl-methylene)-2,2-dimethyl-[1,3]dioxane-4,6-dione (14.2 gm, 0.0572 mol) in ethanol (60 ml) was heated at 85-90° C. for 10 hours. Reaction mixture was cooled to room temperature and filtered. The solid, thus obtained, was washed with ethanol (20 ml) followed by with diethyl ether (50 ml) and suck dried to give 7.2 gm of title compound as a solid.

Workup

customReaction mixture
temperaturewas cooled to room temperature
filtrationfiltered
customThe solid, thus obtained
washwas washed with ethanol (20 ml)
customsuck dried

Sources & evidence

ORD record: ord-1d8e0f44e55846caa74804a84a556536
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822484B2

Linked notes

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