Hydrochloric Acid → 2-(isoxazol-5-yl)benzene-1-sulfonyl chloride(WXC09362)

HRID 1980774Notes

Reaction equation

HRID 1980774 reaction equation
N([O-])=O.[Na+].N[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[O:16][N:15]=[CH:14][CH:13]=1.[ClH:17].[S:18](=[O:20])=[O:19]>O.C(O)(=O)C>[O:16]1[C:12]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[S:18]([Cl:17])(=[O:20])=[O:19])=[CH:13][CH:14]=[N:15]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 134898092-(1,2-Oxazol-5-yl)anilineHCID 23668193Sodium Nitrite

Product 1

HCID 134898112-(isoxazol-5-yl)benzene-1-sulfonyl chloride(WXC09362)

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Conditions

Temperature
10 °C

Procedure

A diazionium salt was prepared by adding a solution of 14.5 g of sodium nitrite in 30 ml of water to a suspension of 32 g of 5-(2-aminophenyl)isoxazole, prepared in Example 3, and 72 ml of concentrated hydrochloric acid in 210 ml of glacial acetic acid cooled at 0° to 5° C. After stirring about 0.4 hour, the diazonium salt suspension was poured in one portion into a mixture consisting of 150 ml of acetic acid, 8.4 g of cupric chloride dihydrate and 60 ml of sulfur dioxide and cooled at 10° C. by an ice-water bath. The mixture was stirred at 10° to 15° C. for 0.2 hour then at about 20° to 30° C. for 3 hours. The suspension was poured into ice-water (about 700 ml) and stirred to form a solid. The mixture was filtered and the solid was washed 3×100 ml of water and suction dried to give 37 g of crude 2-(isoxazol-5-yl)benzenesulfonyl chloride; m.p. 63°-65° C.

Workup

  1. customA diazionium salt was prepared
  2. temperaturecooled at 0° to 5° C
  3. stirringThe mixture was stirred at 10° to 15° C. for 0.2 hour
  4. waitat about 20° to 30° C. for 3 hours
  5. stirringstirred
  6. customto form a solid
  7. filtrationThe mixture was filtered
  8. washthe solid was washed 3×100 ml of water and suction
  9. customdried

Sources & evidence

ORD record
ord-ed744382312340d4a90974edd667775e
Source dataset
uspto-grants-1985_04
Patent number
US04511392

Reaction notes

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