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 44444

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-56678c351f3a4011bd521278eac3355d
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541430B2

Linked notes

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