Tetrahydrofuran → HCID 86605667, compound

HRID 2109480Notes

Reaction equation

HRID 2109480 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]#[N:20])[C:3]=1[S:21][C:22]([F:25])([F:24])[F:23].C(N(CC)CC)C.CCCCCCC.[C:40]([O:43][CH2:44][CH3:45])(=[O:42])[CH3:41].[O:46]1CCCC1>CN(C)C1C=CN=CC=1>[Cl:18][C:8]1[CH:9]=[C:10]([C:14]([F:15])([F:16])[F:17])[CH:11]=[C:12]([Cl:13])[C:7]=1[N:6]1[C:2]([NH:1][C:41]([C:40]([O:43][CH2:44][CH3:45])=[O:42])=[O:46])=[C:3]([S:21][C:22]([F:25])([F:24])[F:23])[C:4]([C:19]#[N:20])=[N:5]1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 8471TriethylamineHCID 9953940Fipronil sulfideHCID 21899848Ethylacetate heptane

Product 1

HCID 86605667HCID 86605667, compound

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

To a solution of 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylthiopyrazole (10.0 g, 23.7 mmol) in tetrahydrofuran was added triethylamine (3.36 g, 33.2 mmol) and 4-dimethylaminopyridine (0.58 g, 4.7 mmol), followed by dropwise addition of ethyl oxalyl chloride (4.21 g, 30.9 mmol) in tetrahydrofuran at 50-70° C. The mixture was heated to reflux for 8 hours. After extractive workup (heptane-ethyl acetate, water, HCl) the title product was obtained (13.9 g).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 8 hours

Sources & evidence

ORD record
ord-359a10c945f144b49dfdeb9769d81470
Source dataset
uspto-grants-2009_04
Patent number
US07514561B2

Reaction notes

Loading…