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Hydrazine hydrate (1:1) → (4,7-Dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalen-6-yl)-(4-trifluoromethoxy-phenyl)-amine

HRID 532605
Notes
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Reaction equation

HRID 532605 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[C:6](=O)[CH2:7][CH2:8][C:2]1=2.[N:10]([C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:15][CH:14]=1)=[C:11]=S.C[Si](C)(C)[Si](C)(C)C.[Li].O.[NH2:34][NH2:35]>C1COCC1.O.C(O)(=O)C>[S:1]1[CH:5]=[CH:4][C:3]2[C:6]3[NH:34][N:35]=[C:11]([NH:10][C:13]4[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:15][CH:14]=4)[C:7]=3[CH2:8][C:2]1=2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 24654Hydrazine hydrate (1:1)HCID 19586324H,5H,6H-cyclopenta[b]thiophen-4-oneHCID 27773384-(Trifluoromethoxy)phenyl isothiocyanateHCID 57425481Lithium hexamethyldisilane

Product 1

HCID 71815515(4,7-Dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalen-6-yl)-(4-trifluoromethoxy-phenyl)-amineYield 33%

Reagents, catalysts & solvents

3
HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5,6-Dihydro-cyclopenta[b]thiophen-4-one (1.0 g, 7.4 mmol) and 1-Isothiocyanato-4-trifluoromethoxy-benzene (1.5 g, 7.2 mmol) in THF (2.0 mL) was added to lithium hexamethyl disilane (7.0 mL, 7.2 mmol) dropwise at room temperature. The reaction mixture was stirred for 8 hr. Hydrazine monohydrate (0.4 mL, 7.9 mmol) and glacial acetic acid (0.5 mL) were added to the reaction mixture, which was then heated at the reflux temperature for 24 hr. The resulting mixture was added to water (30 mL) and then extracted with ethyl acetate. The target product was purified by gravity column chromatography (50% EtOAc in hexane) to give (4,7-Dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalen-6-yl)-(4-trifluoromethoxy-phenyl)-amine as brown solid in 33% yield.

Workup

  1. temperaturewas then heated at the reflux temperature for 24 hr
  2. extractionextracted with ethyl acetate
  3. customThe target product was purified by gravity column chromatography (50% EtOAc in hexane)

Sources & evidence

ORD record
ord-182c1a5722724ec5bb5cb4c2547fd624
Source dataset
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08853207B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes