Cyclohexane → HCID 178462578, compound

HRID 2081169Notes

Reaction equation

HRID 2081169 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([O-:10])(=[O:9])=[O:8])=[CH:3][CH:2]=1.[Cl:12][C:13]1[C:29]([Cl:30])=[CH:28][C:16]2[N+:17]([CH2:26][CH3:27])=[C:18]([CH3:25])[N:19]([CH2:20][C:21]([F:24])([F:23])[F:22])[C:15]=2[CH:14]=1.CCO[CH:34]=[N:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.C1CCCCC1>CN(C)C(=O)C>[C:1]1([CH3:11])[CH:2]=[CH:3][C:4]([S:7]([O-:10])(=[O:8])=[O:9])=[CH:5][CH:6]=1.[NH:35]([CH:34]=[CH:25][C:18]1[N:19]([CH2:20][C:21]([F:23])([F:24])[F:22])[C:15]2[CH:14]=[C:13]([Cl:12])[C:29]([Cl:30])=[CH:28][C:16]=2[N+:17]=1[CH2:26][CH3:27])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

5

Reactant 3

HCID 8078CyclohexaneHCID 111236Methanimidic acid, N-phenyl-, ethyl ester2×HCID 178462745HCID 178462745, compound

Product 1

HCID 178462578HCID 178462578, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
150 °C

Procedure

A slurry of 30 g (0.062 mole) of the 5,6-dichloro-1-ethyl-2-methyl-3-(2,2,2-trifluoroethyl)benzimidazolium p-toluenesulfonate in 150 mL of N,N-dimethylacetamide was treated with 45 g (about 0.3 mole, a large excess) of ethyl iso-formanilide, i.e., N-(ethoxymethylene)aniline, the mixture stirred and heated to 150° C., allowed to cool to 120° C. where it was maintained for 5 minutes, and then allowed to cool slowly to 30° C. The solution was poured into 1.5 L of cyclohexane, stirred, allowed to settle, and the dark reddish oil was separated. The oil was washed with another 500 mL of cyclohexane, separated, treated with 200 mL of methyl ethyl ketone, warmed to a uniform solution and cooled in a freezer to produce a bright yellow-orange solid. The solid was collected by filtration, washed with cold methy ethyl ketone, and dried to produce 23 g melting at 215°-217° C. The mass spec. and NMR spec. are consistent with the assigned structure.

Workup

  1. temperatureto cool to 120° C. where it
  2. temperaturewas maintained for 5 minutes
  3. temperatureto cool slowly to 30° C
  4. customthe dark reddish oil was separated
  5. washThe oil was washed with another 500 mL of cyclohexane
  6. customseparated
  7. additiontreated with 200 mL of methyl ethyl ketone
  8. temperaturewarmed to a uniform solution
  9. temperaturecooled in a freezer
  10. customto produce a bright yellow-orange solid
  11. filtrationThe solid was collected by filtration
  12. washwashed with cold methy ethyl ketone
  13. customdried
  14. customto produce 23 g melting at 215°-217° C

Sources & evidence

ORD record
ord-fae7836603884229a2f42471842e9706
Source dataset
uspto-grants-1993_02
Patent number
US05183813

Reaction notes

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