Sodium Hydroxide → HCID 11163580, compound

HRID 2102783Notes

Reaction equation

HRID 2102783 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[C:10](=O)[CH:9]([CH:12]=O)[CH2:8][CH2:7][C:5]=2[N:6]=1.[N+]([O-])(O)=O.[N+:18]([C:21]1[CH:22]=[C:23]([NH:27][C:28]([NH2:30])=[NH:29])[CH:24]=[CH:25][CH:26]=1)([O-:20])=[O:19].[OH-].[Na+]>COCCO>[CH3:1][C:2]1[S:3][C:4]2[C:10]3[N:30]=[C:28]([NH:27][C:23]4[CH:24]=[CH:25][CH:26]=[C:21]([N+:18]([O-:20])=[O:19])[CH:22]=4)[N:29]=[CH:12][C:9]=3[CH2:8][CH2:7][C:5]=2[N:6]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 248876322-Methyl-7-oxo-4,5,6,7-tetrahydro-1,3-benzothiazole-6-carbaldehydeHCID 1785125133-Nitrophenylguanidine Nitrate

Product 1

HCID 11163580HCID 11163580, compoundYield 5.3%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

A mixture of 2-methyl-7-oxo-4,5,6,7-tetrahydro-benzothiazole-6-carbaldehyde (200 mg, 1 mmol), meta-nitro-phenyl guanidine nitrate (248 mg, 1), NaOH (41 mg, 1 mmol) and 2-methoxyethanol (2 mL) was heated under reflux for 16 h. The reaction mixture was concentrated under vacuum. Flash column chromatography (20% EtOAc:hexane) gave the title compound as a yellow solid (18 mg, 5%): mp 227-228° C. Anal. RP-HPLC: tR 21.9 min (0-60% MeCN, purity 100%). 1H-NMR (DMSO-d6): δ 10.00 (s, 1H, NH), 8.89 (t, 1H, J 2.3, Ph-H), 8.30 (s, 1H, Py-H), 7.92 (ddd, 1H, J 8.3, 2.3, 0.7, Ph-H), 7.66 (ddd, 1H, J 8.3, 2.3, 0.7, Ph-H), 7.44 (t, 1H, J 8.3, Ph-H), 2.90 (m, 4H, CH2—CH2), 2.66 (s, 3H, CH3). 13C-NMR (DMSO-d6): δ 169.16, 159.27, 158.42, 156.05, 155.39, 148.04, 142.02, 129.57, 127.56, 124.22, 117.13, 115.16, 111.91, 24.56, 23.06, 19.48. MS (ESI−): m/z 337.94 (M−H)+.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 16 h
  3. concentrationThe reaction mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-cc92e529f5bc4d4b96e14493921a7f9a
Source dataset
uspto-grants-2009_08
Patent number
US07576091B2

Reaction notes

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