Potassium Carbonate → HCID 21392787, compound

HRID 461837Notes

Reaction equation

HRID 461837 reaction equation
Br[CH:2]([F:28])[C:3]([F:27])([F:26])[S:4][C:5]1[NH:6][C:7]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[N:9]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[F:26][C:3]1([F:27])[S:4][C:5]2=[N:6][C:7]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)=[C:8]([C:10]3[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=3)[N:9]2[CH:2]1[F:28]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 13508095HCID 13508095, compound

Product 1

HCID 21392787HCID 21392787, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.95 g (2 mmoles) of 2-(2-bromo-1,1,2-trifluoroethylthio)-4,5-bis(p-methoxyphenyl) imidazole, 0.6 g (4 mmoles) potassium carbonate and 10 ml dimethylformamide was stirred at 50°-60° for 2 days. The mixture was poured into ice water. The aqueous mixture was extracted three times with ether. The ether was backwashed three times with water, then dried and concentrated on a rotary evaporator. The residue, 0.5 g of crystals, was combined with 0.3 g of product with precipitated from the aqueous layers on standing. The combined crude product was recrystallized from methyl cyclohexane to give 0.7 g of pure product, m.p. 160°-2°. IR: 3.32μ, =CH; 3.50μ, sat. CH; 6.15, 6.54, 6.61μC=C and C=N; strong 8.02μ, aryl C--O; 9.67μ, C--F.H--NMR: 3.8, 3.85δ (2 singlets, 6H); two doublets 5.6, 6.4δ (JHF1 ~61 cps; JHF1 ~7 cps; JHF3 ~0-1 cps, 1H); 2 overlapping A2B2 quartets 6.7-7.6δ (8H). F--NMR: F2 : two doublets, 75.09 and 72.82δ; F3 : two doublets, 86.88 and 89.16δ; F1 : two doublets centered at 139.78δ (JHF1 ~61 cps; JHF2 ~7 cps; JHF3 ~1 cps; JF1F2 ~4 cps; JF1F3 ~8.5 cps; JF2F3 ~213 cps).

Workup

  1. extractionThe aqueous mixture was extracted three times with ether
  2. customdried
  3. concentrationconcentrated on a rotary evaporator
  4. customwith precipitated from the aqueous layers on standing
  5. customwas recrystallized from methyl cyclohexane

Sources & evidence

ORD record
ord-1954697c2e9e480f916e1b7af7648401
Source dataset
uspto-grants-1977_12
Patent number
US04064260

Reaction notes

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