Sodium Carbonate → Glybuthiazol

HRID 1966893Notes

Reaction equation

HRID 1966893 reaction equation
[C:1]([C:5]1[S:9][C:8]([NH:10][S:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20]C(=O)C)=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[N:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[Na+].[Na+]>Cl>[NH2:20][C:17]1[CH:18]=[CH:19][C:14]([S:11]([NH:10][C:8]2[S:9][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[N:6][N:7]=2)(=[O:13])=[O:12])=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 1164242HCID 1164242, compound

Product 1

HCID 10811GlybuthiazolYield 74.5%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Compound 114 (1.0 g, 2.82 mmol) was suspended in 3 N HCl (15 mL) and the suspension heated to reflux for 30 min. Following neutralization with saturated aqueous Na2CO3 solution, the precipitated product was collected by filtration, washed with water (70 mL), and dried under vacuum. The residue was crystallized from MeOH to give the product (655 mg, 2.1 mmol, 74%) as a solid, mp 220-221° C.; 1H NMR (500 MHz, DMSO) δ 1.28 (9, s), 5.91 (2, br s), 6.60 (2, d, J=7.0 Hz), 7.45 (2, d, J=7.0 Hz), 13.95 (1, br s); 13C NMR (125 MHZ, DMSO) δ 29.3, 36.0, 112.6, 127.3, 127.7, 152.5, 166.1, 166.6; MS (LCQ, ESI+) Calculated for C12H17N4O2S2 313.1, found 313.0 (M+H)+; HRMS (FAB+, m/z) Calculated for C12H17N4O2S2 313.0793, found 313.0793 (M+H)+.

Workup

  1. temperaturethe suspension heated
  2. temperatureto reflux for 30 min
  3. filtrationthe precipitated product was collected by filtration
  4. washwashed with water (70 mL)
  5. customdried under vacuum
  6. customThe residue was crystallized from MeOH

Sources & evidence

ORD record
ord-73730b7cacc64c9b95bf5a96822288c3
Source dataset
uspto-grants-2013_04
Patent number
US08420678B2

Reaction notes

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