Ammonium Hydroxide → HCID 13937644, compound

HRID 648858Notes

Reaction equation

HRID 648858 reaction equation
[CH3:1][N:2]([S:4]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([O:15][CH3:16])=[O:14])[C:8]=1[CH2:17][S:18](Cl)(=[O:20])=[O:19])(=[O:6])=[O:5])[CH3:3].[OH-].[NH4+:23]>O1CCCC1>[CH3:1][N:2]([S:4]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([O:15][CH3:16])=[O:14])[C:8]=1[CH2:17][S:18]([NH2:23])(=[O:20])=[O:19])(=[O:6])=[O:5])[CH3:3]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 14153224HCID 14153224, compound

Product 1

HCID 13937644HCID 13937644, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the crude sulfonyl chloride from Example 13 in 150 ml of tetrahydrofuran was cooled to 0° and treated with 7.3 ml of concentrated aqueous ammonium hydroxide. The resulting suspension was allowed to warm to room temperature. Removal of the solvent in vacuo gave an oily residue which was triturated with 300 ml water. The precipitate was collected by filtration, washed with n-butyl chloride and dried to yield 9.3 g of 2-[(N,N-dimethylamino)sulfonyl]-6-(methoxycarbonyl)phenylmethanesulfonamide as a light yellow solid, m.p. 133°-142°; IR(nujol): 3400, 3310, 1720 cm-1 ; NMR (CDCl3 /DMSO-d6): δ 2.6 (6H, s, SO2N(CH3)2), 3.8 (3H, s, CO2CH3), 5.35 (2H, s, --CH2 --), 5.3-5.9 (2H, br s, NH2), 7.4-8.3 (3H, m).

Workup

  1. customRemoval of the solvent in vacuo
  2. customgave an oily residue which
  3. customwas triturated with 300 ml water
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with n-butyl chloride
  6. customdried

Sources & evidence

ORD record
ord-27854aa5627b469f93c6224bf053683f
Source dataset
uspto-grants-1988_04
Patent number
US04737185

Reaction notes

Loading…