Hydrochloric Acid → HCID 28788197, compound

HRID 509298Notes

Reaction equation

HRID 509298 reaction equation
[CH3:1][N:2]([CH3:18])[S:3]([NH:6][CH2:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14]C)=[O:13])=[CH:10][CH:9]=1)(=[O:5])=[O:4].[OH-].[K+].Cl>C1COCC1>[CH3:1][N:2]([CH3:18])[S:3]([NH:6][CH2:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=1)(=[O:5])=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 35326857HCID 35326857, compound

Product 1

HCID 28788197HCID 28788197, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Methyl 4-({[(dimethylamino)sulfonyl]amino}methyl)benzoate (0.25 g, 0.918 mmol) was dissolved in THF (5 ml). Potassium hydroxide (5 ml, 10.00 mmol) was added. The reaction was heated to 50° C. for 3.5 h, until reaction was complete as indicated by LCMS. Hydrochloric acid (5 ml, 2N) was added. The reaction was concentrated under reduced pressure. The resulting material was dissolved in organic solvent DCM/MeOH and washed with brine. The aqueous layer was extracted with DCM/MeOH two times. The combined organic layers were dried over Na2SO4, filtered, and concentrated. 1H NMR (d6-DMSO, 600 MHz) δ 12.88 (s, 1H), 7.88 (d, J=8.5 Hz, 2H), 7.76 (t, J=6.5 Hz, 1H), 7.42 (d, J=8.5 Hz, 2H), 4.14 (d, J=6.5 Hz, 2H), 2.59 (s, 6H). MS: cal'd 259 (MH+), exp 259 (MH+).

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. dissolutionThe resulting material was dissolved in organic solvent DCM/MeOH
  3. washwashed with brine
  4. extractionThe aqueous layer was extracted with DCM/MeOH two times
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b07895b67c6a42a195d7ddc6ecb58afe
Source dataset
uspto-grants-2015_08
Patent number
US09096559B2

Reaction notes

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