Ethylamine → HCID 14093323, compound

HRID 986540Notes

Reaction equation

HRID 986540 reaction equation
Cl[S:2]([OH:5])(=O)=[O:3].[C:6]1([CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[OH-].[Na+].[CH2:20]([NH2:22])[CH3:21]>O>[CH2:20]([NH:22][S:2]([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)(=[O:5])=[O:3])[CH3:21]

Participants

6

Reactant 4

HCID 6341EthylamineHCID 13229CyclohexylbenzeneHCID 14798Sodium HydroxideHCID 24638Chlorosulfonic acid2×

Product 1

HCID 14093323HCID 14093323, compoundYield 28.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A 1 liter flask equipped as in Example 2 was charged with 254 gms (2.18 moles) of chlorosulfonic acid, and then 100 gms (0.62 moles) of phenylcyclohexane was added to the stirred chlorosulfonic acid over a 11/2 hour period at 25° C. to 30° C. under N2. The mixture was stirred at 25° C. under N2 for 4 hours and then it was added to a mixture of 376 gms of 50 percent sodium hydroxide (4.7 moles), 500 mls of deionized water and 40 gms (0.62 moles) of 70 percent ethylamine at 40° C. to 50° C. over a 2 hour period at a pH above 10. The cooled reaction mixture was filtered to isolate a tan solid which was then washed with water and recrystallized from cyclohexane to give 48.7 gms (28.9% yield), m.p. 100°-101.5° C., proton NMR consistent with N-ethyl cyclohexylbenzene sulfonamide structure.

Workup

  1. customA 1 liter flask equipped as in Example 2
  2. customThe cooled reaction mixture
  3. filtrationwas filtered
  4. customto isolate a tan solid which
  5. washwas then washed with water
  6. customrecrystallized from cyclohexane

Sources & evidence

ORD record
ord-b69629d6dedc40e88625a6746816121b
Source dataset
uspto-grants-1987_12
Patent number
US04713489

Reaction notes

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