Bis(2,2,2-trichloroethyl) hydrazine-1,2-dicarboxylate → Bis(2,2,2-trichloroethyl) 1-(2,3-dihydrobenzofuran-5-yl)hydrazine-1,2-dicarboxylate

HRID 384308Notes

Reaction equation

HRID 384308 reaction equation
O1C2C=CC=CC=2CC1.[O:10]1[C:14]2[CH:15]=[CH:16][C:17]([N:19]([C:29]([O:31][CH2:32][C:33]([Cl:36])([Cl:35])[Cl:34])=[O:30])[NH:20][C:21]([O:23][CH2:24][C:25]([Cl:28])([Cl:27])[Cl:26])=[O:22])=[CH:18][C:13]=2[CH2:12][CH2:11]1.N(C(OCC(Cl)(Cl)Cl)=O)NC(OCC(Cl)(Cl)Cl)=O>ClCCl.[Cl-].[Zn+2].[Cl-]>[O:10]1[C:14]2[CH:15]=[CH:16][C:17]([N:19]([C:29]([O:31][CH2:32][C:33]([Cl:34])([Cl:35])[Cl:36])=[O:30])[NH:20][C:21]([O:23][CH2:24][C:25]([Cl:27])([Cl:28])[Cl:26])=[O:22])=[CH:18][C:13]=2[CH2:12][CH2:11]1

Participants

5

Reactant 2

HCID 350435Bis(2,2,2-trichloroethyl) hydrazine-1,2-dicarboxylateHCID 86648897Bis(2,2,2-trichloroethyl) 1-(2,3-dihydrobenzofuran-5-yl)hydrazine-1,2-dicarboxylate 2,3-Dihydro-benzofuran

Product 1

HCID 10505571Bis(2,2,2-trichloroethyl) 1-(2,3-dihydrobenzofuran-5-yl)hydrazine-1,2-dicarboxylateYield 96.6%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

Bis(2,2,2-trichloroethyl) 1-(2,3-dihydrobenzofuran-5-yl)hydrazine-1,2-dicarboxylate 2,3-Dihydro-benzofuran 7a (0.6 mL, 5.32 mmol), bis(2,2,2-trichloroethyl) hydrazine-1,2-dicarboxylate (1.96 g, 5.15 mmol) and zinc chloride (920 mg, 6.76 mmol) were dissolved in 40 mL of dichloromethane. The reaction was reacted overnight at room temperature and monitored by TLC until the disappearance of the starting materials. Then the mixture was purified by silica gel column chromatography to obtain the title compound bis(2,2,2-trichloroethyl) 1-(2,3-dihydrobenzofuran-5-yl)hydrazine-1,2-dicarboxylate 7b (2.5 g, yield 96.6%) as a white solid.

Workup

  1. customThe reaction was reacted overnight at room temperature
  2. customThen the mixture was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3a13d733d8684b419f183f2627834bef
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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