Ammonia → 2-[(2-Methoxyethyl)sulfanyl]benzene-1-sulfonamide

HRID 370614Notes

Reaction equation

HRID 370614 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][S:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1N.Cl.N([O-])=O.[Na+].[S:18](=[O:20])=[O:19].[NH3:21]>O.C(O)(=O)C>[CH3:1][O:2][CH2:3][CH2:4][S:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[S:18]([NH2:21])(=[O:20])=[O:19]

Participants

8

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 4575136HCID 4575136, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 136459362-[(2-Methoxyethyl)sulfanyl]benzene-1-sulfonamideYield 68%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Procedure

To a suspension of 2-(2-methoxyethylthio)benzenamine (91.5 g, 0.500 mol) in a mixture of concentrated hydrochloric acid (175 ml) and glacial acetic acid (80 ml) was added a solution of sodium nitrite (39.3 g, 0.550 mol) in water (75 ml) at -5° to 0°. The solution was stirred at 0° for 1/2 hour and then poured, in several portions, into a mixture of cupric chloride dihydrate (10.0 g, 0.059 mol) and liquid sulfur dioxide (77.5 ml, 1.76 mol), in glacial acetic acid (500 ml) at 0°. The resulting solution was stirred at 0° for one hour and then allowed to warm to room temperature. After four hours, ice-water (2000 ml) was added and the resulting oil was extracted into 1-chlorobutane (4×500 ml). The organic extracts were washed with water (5×500 ml) and saturated sodium bicarbonate (until neutral), dried (MgSO4), filtered and reduced in volume to 1000 ml. The sulfonyl chloride solution was cooled to 0° under nitrogen and treated with liquid anhydrous ammonia (50 ml, 2.0 mol). After 1 hour at 0°, the mixture was allowed to warm to room temperature and stirred for 21/2 hours. The reaction mixture was filtered and the resulting solid washed with 1-chlorobutane and water. 2-(2-methoxyethylthio)benzenesulfonamide (84 g, 68%) was obtained as a light-orange solid: m.p. 127°-130°.

Workup

  1. stirringThe resulting solution was stirred at 0° for one hour
  2. waitAfter four hours
  3. extractionthe resulting oil was extracted into 1-chlorobutane (4×500 ml)
  4. washThe organic extracts were washed with water (5×500 ml) and saturated sodium bicarbonate (until neutral)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. temperatureThe sulfonyl chloride solution was cooled to 0° under nitrogen
  8. waitAfter 1 hour at 0°
  9. temperatureto warm to room temperature
  10. stirringstirred for 21/2 hours
  11. filtrationThe reaction mixture was filtered
  12. washthe resulting solid washed with 1-chlorobutane and water

Sources & evidence

ORD record
ord-c8d6557ef612499e8b05d9801957e95f
Source dataset
uspto-grants-1985_07
Patent number
US04528024

Reaction notes

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