Hydrochloric Acid → 5-(4-Chloro-3-chlorosulfonylphenyl)-5-hydroxy-1-methyl-2-pyrrolidone

HRID 231832

Reaction equation

HRID 231832 reaction equation
N([O-])=O.[Na+].N[C:6]1[CH:7]=[C:8]([C:13]2([OH:20])[N:17]([CH3:18])[C:16](=[O:19])[CH2:15][CH2:14]2)[CH:9]=[CH:10][C:11]=1[Cl:12].[S:21](=[O:23])=[O:22].[ClH:24]>O.C(O)(=O)C.O.O.[Cu](Cl)Cl>[Cl:12][C:11]1[CH:10]=[CH:9][C:8]([C:13]2([OH:20])[N:17]([CH3:18])[C:16](=[O:19])[CH2:15][CH2:14]2)=[CH:7][C:6]=1[S:21]([Cl:24])(=[O:23])=[O:22]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 142568035-(3-Amino-4-chlorophenyl)-5-hydroxy-1-methylpyrrolidin-2-oneHCID 23668193Sodium Nitrite

Product 1

HCID 142568045-(4-Chloro-3-chlorosulfonylphenyl)-5-hydroxy-1-methyl-2-pyrrolidone

Reagents, catalysts & solvents 3

HCID 61482Cupric chloride dihydrateCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 9.9 g of sodium nitrite in 60 ml of water is metered into, below the surface of, a solution of 30.5 g of 5-(3-amino-4-chlorophenyl)-5-hydroxy-1-methyl-2-pyrrolidone in 300 ml of half-concentrated hydrochloric acid at at 0° to 5° C. The reaction mixture is stirred while cooling for a further 10 min, and then a mixture of 15.2 g of copper(II)chloride dihydrate and 450 ml of a saturated solution of sulfur dioxide in glacial acetic acid is added in portions. The mixture is stirred for a further 30 min, and then the sulfonyl chloride is precipitated by addition of water, and the crystals are filtered off. Melting point 137°-139° C.

Workup

  1. customat at 0° to 5° C
  2. temperaturewhile cooling for a further 10 min
  3. additionis added in portions
  4. stirringThe mixture is stirred for a further 30 min
  5. customthe sulfonyl chloride is precipitated by addition of water
  6. filtrationthe crystals are filtered off

Sources & evidence

ORD record
ord-d3003e71854a4252b620381bf1185b50
Source dataset
uspto-grants-1989_07
Patent number
US04849444

Linked notes

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