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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
Notes
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Reaction equation

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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 180462-Amino-4,5,6,7-tetrahydrobenzothiazoleHCID 136798125-[Bis(ethylsulfanyl)methylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 671171072-methylsulfanyl-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-1,4a-diaza-fluorene-3-carboxylic acidYield 46.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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

  1. customReaction mixture
  2. temperaturewas cooled to room temperature
  3. filtrationfiltered
  4. customThe solid, thus obtained
  5. washwas washed with ethanol (20 ml)
  6. customsuck dried

Sources & evidence

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

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes