Ammonia → 2-(Aminosulfonyl)-N-methoxybenzenecarboximidoyl chloride
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
Product 1
Reagents, catalysts & solvents 1
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): ppm 4.2(s, 3H, OCH3) 6.6 (bs, 2H, NH2), 7.8 (m, 4H, Ar).
Workup
- customthe suspension was purged with N2
- customto remove excess ammonia
- customevaporated at less than 30° C. under vacuum
- additionAfter adding ice-water to the residue the suspension
- extractionwas extracted with methylene chloride
- dry with materialdried (MgSO4)
- customevaporated under vacuum
- customThe residue was triturated with hexane
Sources & evidence
- ORD record
- ord-10f852e924fd44dabf2c762cc8ca953a
- Source dataset
- uspto-grants-1991_02
- Patent number
- US04995901
Reaction notes
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