Ammonia → 5-Chloro-2-methylbenzenesulfonamide

HRID 1285273Notes

Reaction equation

HRID 1285273 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:12])=[C:6]([S:8](Cl)(=[O:10])=[O:9])[CH:7]=1.[NH3:13]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:12])=[C:6]([S:8]([NH2:13])(=[O:10])=[O:9])[CH:7]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 1004154-Chlorotoluene-2-sulphonyl chloride

Product 1

HCID 2566195-Chloro-2-methylbenzenesulfonamideYield 70.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3810.5 g of 5-chloro-2-methylbenzenesulfonyl chloride in 10.8 L of tetrahydrofuran was cooled to 0°-5° C. and 720 g of anhydrous ammonia was added while maintaining the temperature at 0°-5° C. When addition was complete, the suspension was stirred several hours at 0°-5° C., then allowed to warm to ambient temperature overnight. The precipitated ammonium chloride was filtered and washed with tetrahydrofuran. The filtrate was concentrated in vacuo until solids were formed. The solids were collected, washed with 1-chlorobutane and dried to give 2449 g of the title compound, m.p. 142°-145° C.

Workup

  1. temperaturewhile maintaining the temperature at 0°-5° C
  2. additionWhen addition
  3. filtrationThe precipitated ammonium chloride was filtered
  4. washwashed with tetrahydrofuran
  5. concentrationThe filtrate was concentrated in vacuo until solids
  6. customwere formed
  7. customThe solids were collected
  8. washwashed with 1-chlorobutane
  9. customdried

Sources & evidence

ORD record
ord-409cdd69452244c0bc5f0cd0678bba54
Source dataset
uspto-grants-1986_01
Patent number
US04566898

Reaction notes

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