Thionyl Chloride → 4-(3,4-Bis(benzyloxy)-5-nitrophenyl)-5-(2-(trifluoromethyl)pyridin-3-yl)-1,2,3-thiadiazole

HRID 62019Notes

Reaction equation

HRID 62019 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11](/[C:26](=[N:38]\[NH:39]C(OCC)=O)/[CH2:27][C:28]2[C:29]([C:34]([F:37])([F:36])[F:35])=[N:30][CH:31]=[CH:32][CH:33]=2)[CH:12]=[C:13]([N+:23]([O-:25])=[O:24])[C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:45](Cl)(Cl)=O>>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:26]2[N:38]=[N:39][S:45][C:27]=2[C:28]2[C:29]([C:34]([F:37])([F:36])[F:35])=[N:30][CH:31]=[CH:32][CH:33]=2)[CH:12]=[C:13]([N+:23]([O-:25])=[O:24])[C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 87588773ethyl N-[(Z)-[1-[3-nitro-4,5-bis(phenylmethoxy)phenyl]-2-[2-(trifluoromethyl)-3-pyridinyl]ethylidene]amino]carbamate

Product 1

HCID 687015364-(3,4-Bis(benzyloxy)-5-nitrophenyl)-5-(2-(trifluoromethyl)pyridin-3-yl)-1,2,3-thiadiazole

Procedure

A mixture of (Z)-ethyl 2-(1-(3,4-bis(benzyloxy)-5-nitrophenyl)-2-(2-(trifluoromethyl)pyridin-3-yl)ethylidene)hydrazinecarboxylate (0.388 g, 0.64 mmol), in thionyl chloride (2 mL) was refluxed until no more starting material was detected. Excess of solvent was removed and the residue was purified by chromatography over silica gel using a mixture of dichloromethane/ethanol as eluent. Homogeneous fractions were pooled and evaporated to afford 4-(3,4-bis(benzyloxy)-5-nitrophenyl)-5-(2-(trifluoromethyl)pyridin-3-yl)-1,2,3-thiadiazole, 0.184 g (51%).

Workup

  1. customExcess of solvent was removed
  2. customthe residue was purified by chromatography over silica gel using
  3. additiona mixture of dichloromethane/ethanol as eluent
  4. customevaporated

Sources & evidence

ORD record
ord-09e17e318ad14de29ab1e5b92df6c9de
Source dataset
uspto-grants-2016_09
Patent number
US09446012B2

Reaction notes

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