Stannous chloride dihydrate → 2,5-Bis-(3,5-bis-trifluoromethyl-phenyl)-thiophene-3,4-diamine

HRID 1671848Notes

Reaction equation

HRID 1671848 reaction equation
[F:1][C:2]([F:39])([F:38])[C:3]1[CH:4]=[C:5]([C:13]2[S:14][C:15]([C:24]3[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[C:26]([C:34]([F:37])([F:36])[F:35])[CH:25]=3)=[C:16]([N+:21]([O-])=O)[C:17]=2[N+:18]([O-])=O)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.BrC1SC(Br)=C([N+]([O-])=O)C=1[N+]([O-])=O.FC(F)(F)C1C=C([Sn](CCCC)(CCCC)CCCC)C=C(C(F)(F)F)C=1.O.O.[Sn](Cl)Cl>C(O)C>[F:12][C:9]([F:10])([F:11])[C:7]1[CH:6]=[C:5]([C:13]2[S:14][C:15]([C:24]3[CH:29]=[C:28]([C:30]([F:31])([F:32])[F:33])[CH:27]=[C:26]([C:34]([F:37])([F:36])[F:35])[CH:25]=3)=[C:16]([NH2:21])[C:17]=2[NH2:18])[CH:4]=[C:3]([C:2]([F:39])([F:38])[F:1])[CH:8]=1

Participants

6

Reactant 4

HCID 61436Stannous chloride dihydrateHCID 2570242,5-Dibromo-3,4-dinitrothiopheneHCID 121440523,5-Bis-trifluoromethyl-phenyl-tributyl-stannaneHCID 576099972,5-Bis-(3,5-bis-trifluoromethyl-phenyl)-3,4-dinitro-thiophene

Product 1

HCID 576099842,5-Bis-(3,5-bis-trifluoromethyl-phenyl)-thiophene-3,4-diamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2,5-Bis-(3,5-bis-trifluoromethyl-phenyl)-3,4-dinitro-thiophene was made by Stille coupling reaction of 2,5-dibromo-3,4-dinitro-thiophene and 3,5-bis-trifluoromethyl-phenyl-tributyl-stannane. It was reduced with tin (II) chloride dihydrate in ethanol to give 2,5-bis-(3,5-bis-trifluoromethyl-phenyl)-thiophene-3,4-diamine. The diamine was reacted with hexaketocyclohexane octahydrate to give compound A. The product is a red-brown solid. It is soluble in common organic solvents such as dichloromethane and THF. It was purified by flash chromatography on silica gel and crystallization in ethanol. The purified product had elemental analysis data consistent with the formula for the desired compound.

Sources & evidence

ORD record
ord-d05ca64b026d46a199ca0f1fe80092c1
Source dataset
uspto-grants-2011_08
Patent number
US07994423B2

Reaction notes

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