HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Hydrazine hydrate (1:1) → (4,7-Dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalen-6-yl)-(2-trifluoromethyl-phenyl)-amine

HRID 532599
Notes
Print preview

Reaction equation

HRID 532599 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][CH:16]=[CH:15][C:14]=1[C:19]([F:22])([F:21])[F:20])=[C:11]=S.C[Si](C)(C)[Si](C)(C)C.[Li].O.[NH2:33][NH2:34]>C1COCC1.O.C(O)(=O)C>[S:1]1[CH:5]=[CH:4][C:3]2[C:6]3[NH:33][N:34]=[C:11]([NH:10][C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=4[C:19]([F:22])([F:21])[F:20])[C:7]=3[CH2:8][C:2]1=2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 24654Hydrazine hydrate (1:1)HCID 7371622-(Trifluoromethyl)phenyl isothiocyanateHCID 19586324H,5H,6H-cyclopenta[b]thiophen-4-oneHCID 57425481Lithium hexamethyldisilane

Product 1

HCID 71815513(4,7-Dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalen-6-yl)-(2-trifluoromethyl-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-2-trifluoromethyl-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 a (4,7-Dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalen-6-yl)-(2-trifluoromethyl-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-352017fda4724c919f9e49b6ceae5fef
Source dataset
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08853207B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes