Ammonia → N-(Aminocarbonyl)-2,3-dichlorobenzenesulfonamide

HRID 236521Notes

Reaction equation

HRID 236521 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[S:9]([N:12]=[C:13]=[O:14])(=[O:11])=[O:10].[NH3:15]>O1CCCC1>[NH2:15][C:13]([NH:12][S:9]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([Cl:8])[C:2]=1[Cl:1])(=[O:10])=[O:11])=[O:14]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 138527082,3-Dichlorobenzenesulfonyl isocyanate

Product 1

HCID 13852713N-(Aminocarbonyl)-2,3-dichlorobenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 10.0 g of 2,3-dichlorobenzenesulfonyl isocyanate in 200 mL of dry tetrahydrofuran was cooled to 0° C. and treated with 5.0 mL of anhydrous liquid ammonia, added in a dropwise manner at a rate that maintained the temperature between 0° and 10° C. The resultant white mixture was allowed to warm to room temperature and was stirred overnight. The precipitate was collected by filtration, dissolved in 250 mL of water, and acidified with concentrated hydrochloric acid to yield a white solid. Filtration and air drying gave 7.0 g of the title compound, m.p. 197°-200° C.; NMR (DMSO-d6): δ6.0-6.8 (br s, 2H), 7.6 (t, 1H), 7.8-8.1 (m, 2H), 11.1 (br s, 1H); IR (nujol): 1690 cm-1.

Workup

  1. additionadded in a dropwise manner at a rate that
  2. temperaturemaintained the temperature between 0° and 10° C
  3. filtrationThe precipitate was collected by filtration
  4. dissolutiondissolved in 250 mL of water
  5. customto yield a white solid
  6. filtrationFiltration and air
  7. customdrying

Sources & evidence

ORD record
ord-4e3d0912f6934d6184133f7a64d678af
Source dataset
uspto-grants-1987_02
Patent number
US04645527

Reaction notes

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