Potassium Iodide → HCID 15124793, compound

HRID 466537Notes

Reaction equation

HRID 466537 reaction equation
Cl[CH2:2][CH2:3][N:4]([CH2:15][CH2:16][CH2:17]Cl)[S:5]([C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)(=[O:7])=[O:6].[CH3:19][C:20]1[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][C:21]=1[NH2:27].C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+].C1(O)CCCCC1>O>[CH3:19][C:20]1[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][C:21]=1[N:27]1[CH2:17][CH2:16][CH2:15][N:4]([S:5]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)(=[O:7])=[O:6])[CH2:3][CH2:2]1

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 68932,3-DimethylanilineHCID 7966CyclohexanolHCID 10340Sodium CarbonateHCID 19095623HCID 19095623, compound

Product 1

HCID 15124793HCID 15124793, compoundYield 53.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 93 parts of N-(2-chloroethyl)-N-(3-chloropropyl)-4-methylbenzenesulfonamide, 30.3 parts of 2,3-dimethylbenzenamine, 63.6 parts of sodium carbonate, 1 part of potassium iodide and 240 parts of cyclohexanol was stirred and refluxed over weekend using a water separator. After cooling, the reaction mixture was poured into water. The product was extracted with methylbenzene. The extract was washed twice with water, dried, filtered and evaporated. The residue was crystallized from 2-propanol and a small amount of tetrahydrofuran. The product was filtered off and dried, yielding 47.8 parts (53.3%) of 1-(2,3-dimethylphenyl)hexahydro-4-[(4-methylphenyl)sulfonyl]-1H-1,4-diazepine; mp. 86.2° C. (intermediate 7).

Workup

  1. temperaturerefluxed over weekend
  2. temperatureAfter cooling
  3. extractionThe product was extracted with methylbenzene
  4. washThe extract was washed twice with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was crystallized from 2-propanol
  9. filtrationThe product was filtered off
  10. customdried

Sources & evidence

ORD record
ord-9b1d7dae9e5b40cbb933e889743c7a08
Source dataset
uspto-grants-1992_10
Patent number
US05157035

Reaction notes

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