Ammonia → 2-(Aminosulfonyl)-N-methoxybenzenecarboximidoyl chloride

HRID 1164725Notes

Reaction equation

HRID 1164725 reaction equation
Cl[S:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]([Cl:15])=[N:12][O:13][CH3:14])(=[O:4])=[O:3].[NH3:16]>O1CCCC1>[NH2:16][S:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]([Cl:15])=[N:12][O:13][CH3:14])(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 537421902-(Chlorosulfonyl)-N-methoxybenzenecarboximidoyl chloride

Product 1

HCID 540187652-(Aminosulfonyl)-N-methoxybenzenecarboximidoyl chloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-30 °C

Procedure

To a solution of the oil prepared in Example 3 in 100 ml of tetrahydrofuran, cooled at -30° C. with external cooling, was added dropwise 1.7 ml of ammonia. After stirring at -30° C. for about 15 minutes, the suspension was purged with N2 to remove excess ammonia, then evaporated at less than 30° C. under vacuum. After adding ice-water to the residue, the suspension was extracted with methylene chloride, dried (MgSO4) and evaporated under vacuum. The residue was triturated with hexane to yield 2.5 g of the subject compound as a crude solid, m.p. 155° to 158° C., NMR(CDCl3 +DMSO):

Workup

  1. customthe suspension was purged with N2
  2. customto remove excess ammonia
  3. customevaporated at less than 30° C. under vacuum
  4. additionAfter adding ice-water to the residue
  5. extractionthe suspension was extracted with methylene chloride
  6. dry with materialdried (MgSO4)
  7. customevaporated under vacuum
  8. customThe residue was triturated with hexane

Sources & evidence

ORD record
ord-20eb8f2542af4f6a84e953a65a25d441
Source dataset
uspto-grants-1990_03
Patent number
US04906282

Reaction notes

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