Triethylamine → HCID 89445139, compound

HRID 1522778Notes

Reaction equation

HRID 1522778 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](/[C:9](/[C:26]([F:29])([F:28])[F:27])=[CH:10]\[C:11]([C:13]2[CH:14]=[CH:15][C:16]([N:21]3[CH:25]=[N:24][CH:23]=[N:22]3)=[C:17]([CH:20]=2)[C:18]#[N:19])=[O:12])[CH:5]=[C:6]([Cl:8])[CH:7]=1.C(O)(=[S:32])C.C(N(CC)CC)C>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([SH:32])([C:26]([F:28])([F:27])[F:29])[CH2:10][C:11]([C:13]2[CH:14]=[CH:15][C:16]([N:21]3[CH:25]=[N:24][CH:23]=[N:22]3)=[C:17]([CH:20]=2)[C:18]#[N:19])=[O:12])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 67377109HCID 67377109, compoundHCID 178418634HCID 178418634, compound2×

Product 1

HCID 89445139HCID 89445139, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 5-[(E)-3-(3,5-Dichloro-phenyl)-4,4,4-trifluoro-but-2-enoyl]-2-[1,2,4]triazol-1-yl-benzonitrile (100 mg) was added thioacetic acid (6 eq.) and triethylamine (4 μL). To dissolve the suspension more thioacetic acid (400 μL) was added. The solution was stirred under argon at room temperature for 20 hours. To this mixture was added a minimum of dichloromethane and then isolute. The suspension was evaporated under vacuo. The residue was purified by chromatography on silica gel (eluent: cyclohexane/dichloromethane) to give 5-[3-(3,5-Dichloro-phenyl)-4,4,4-trifluoro-3-mercapto-butyryl]-2-[1,2,4]triazol-1-yl-benzonitrile (108 mg).

Workup

  1. additionwas added
  2. customThe suspension was evaporated under vacuo
  3. customThe residue was purified by chromatography on silica gel (eluent: cyclohexane/dichloromethane)

Sources & evidence

ORD record
ord-af3687f83ae64b4e86d7042c68b22857
Source dataset
uspto-grants-2015_07
Patent number
US09078444B2

Reaction notes

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