Potassium Hydroxide → HCID 16063314, compound

HRID 1917260Notes

Reaction equation

HRID 1917260 reaction equation
[CH2:1]([N:8]1[CH2:17][CH2:16][C:15]2[C:14]([C:18]3[CH:19]=[C:20]([CH:23]=O)[S:21][CH:22]=3)=[N:13][C:12]([CH:25]([CH3:27])[CH3:26])=[N:11][C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.NN.[OH-].[K+]>C(O)CO.O>[CH2:1]([N:8]1[CH2:17][CH2:16][C:15]2[C:14]([C:18]3[CH:19]=[C:20]([CH3:23])[S:21][CH:22]=3)=[N:13][C:12]([CH:25]([CH3:27])[CH3:26])=[N:11][C:10]=2[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 86762198HCID 86762198, compound

Product 1

HCID 16063314HCID 16063314, compoundYield 65.9%

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 962WaterSolvent

Conditions

Temperature
200 °C

Procedure

To a solution of the product of Step A (0.230 g) in ethylene glycol was added hydrazine hydrate (0.1 mL). The mixture was heated at 200° C. for 1 h, then KOH (0.150 g) was added and the heating continued for 6 h. The mixture was allowed to cool then was diluted with water and extracted with Et2O. The combined organic extracts were dried and concentrated to 0.210 g of pale yellow solid. Chromatography on SiO2 (EtOAc/hexanes) afforded 0.146 g of the title compound. MS (ESI): exact mass calcd. for C22H25N3S, 363.18; found m/z 364.4 [M+H]+. 1H NMR (MeOH-d4): 7.85-7.84 (m, 1H), 7.65-7.63 (m, 2H), 7.56-7.55 (m, 3H), 7.37-7.36 (m, 1H), 4.60 (br s, 2H), 4.44 (br s, 2H), 3.46-3.32 (m, 2H), 3.22-3.17 (m, 1H), 2.55 (s, 3H), 1.34 (d, J=7.2, 6H).

Workup

  1. temperatureto cool
  2. extractionextracted with Et2O
  3. customThe combined organic extracts were dried
  4. concentrationconcentrated to 0.210 g of pale yellow solid

Sources & evidence

ORD record
ord-2a0c401f3b204496a7306e545a9a2c6b
Source dataset
uspto-grants-2013_12
Patent number
US08618288B2

Reaction notes

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