tert-Butanol → HCID 178488067, compound

HRID 1655396Notes

Reaction equation

HRID 1655396 reaction equation
CC(C)([O-])C.[K+].[N:7]#[C:8][NH2:9].C(O)(C)(C)C.[CH3:15][O:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][C:21]([CH3:26])=[C:20]2/[CH:27]=[C:28]1/[C:29](=[O:35])[N:30]=[C:31](SC)[S:32]/1>O>[CH3:15][O:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][C:21]([CH3:26])=[C:20]2/[CH:27]=[C:28]1/[C:29](=[O:35])[N:30]=[C:31]([NH:9][C:8]#[N:7])[S:32]/1

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 9864CyanamideHCID 23665647Potassium tert-butoxideHCID 178488069HCID 178488069, compound

Product 1

HCID 178488067HCID 178488067, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a room temperature suspension of potassium t-butoxide (73 mg, 0.65 mmols) and cyanamide (96 mg, 2.27 mmols) in mL of t-butanol is added (Z)-5-[(5-methoxy-2-methyl-1H-indol-3-yl)methylene]-2-(methylthio)-4(5H)-thiazolone (146 mg, 0.46 mmols). The mixture is heated at reflux for 5 minutes, then cooled to room temperature. The mixture is poured into 50 mL of water and the orange solution is washed with diethyl ether. The layers are separated and the aqueous layer is acidified with 10% aqueous hydrochloric acid. The orange solid is collected by filtration, washing with water to give 106 mg (74%) of (Z)-[4,5-dihydro-5-[(5-methoxy-2-methyl-1H-indol-3-yl)methylene]-4-oxo-2-thiazolyl]cyanamide; mp>300.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 5 minutes
  3. washthe orange solution is washed with diethyl ether
  4. customThe layers are separated
  5. filtrationThe orange solid is collected by filtration
  6. washwashing with water

Sources & evidence

ORD record
ord-17f5f417d98f4d54bdc4394bd8170b44
Source dataset
uspto-grants-1993_10
Patent number
US05250552

Reaction notes

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