Ammonia → Methyl 3-(aminosulfonyl)-5-[(dipropylamino)carbonyl]-Benzoate

HRID 1987741Notes

Reaction equation

HRID 1987741 reaction equation
Cl[S:2]([C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([C:15]([N:17]([CH2:21][CH2:22][CH3:23])[CH2:18][CH2:19][CH3:20])=[O:16])[CH:14]=1)[C:8]([O:10][CH3:11])=[O:9])(=[O:4])=[O:3].[NH3:24]>C1COCC1>[NH2:24][S:2]([C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([C:15]([N:17]([CH2:21][CH2:22][CH3:23])[CH2:18][CH2:19][CH3:20])=[O:16])[CH:14]=1)[C:8]([O:10][CH3:11])=[O:9])(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 22593631Methyl 3-(chlorosulfonyl)-5-[(dipropylamino)carbonyl]-Benzoate

Product 1

HCID 22593632Methyl 3-(aminosulfonyl)-5-[(dipropylamino)carbonyl]-Benzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-(chlorosulfonyl)-5-[(dipropylamino)carbonyl]benzoate (XXXVII, PREPARATION 11, 0.100 g, 0.300 mmol) in dry THF (3 mL) is added ammonia (7 N solution in methanol, 0.214 mL, 1.50 mmol). The mixture is stirred for 18 hours and solvent is then removed. The residue is partitioned between ethyl acetate and water. The organic phase is separate and washed with saline, dried over anhydrous sodium sulfate, filtered, and concentrated to give the title compound, NMR (300 MHz, CDCl3) delta 8.45, 8.07, 8.01, 6.05, 3.93, 3.44, 3.09, 1.67, 1.52, 0.96 and 0.73; MS (ESI+) for C12H22N2O5S m/z (M+H)+=343.3.

Workup

  1. customsolvent is then removed
  2. customThe residue is partitioned between ethyl acetate and water
  3. customThe organic phase is separate
  4. washwashed with saline
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b4800d6469734220955b8a9caafefe09
Source dataset
uspto-grants-2009_06
Patent number
US07553831B2

Reaction notes

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