Propargyl bromide → HCID 22158382, compound

HRID 1073219Notes

Reaction equation

HRID 1073219 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH2:12]([Br:15])[C:13]#[CH:14]>C(O)CCC>[BrH:15].[NH:1]=[C:2]1[N:6]([CH2:14][C:13]#[CH:12])[C:5]2[CH:7]=[CH:8][C:9]([F:11])=[CH:10][C:4]=2[S:3]1

Participants

4

Reactant 2

HCID 7842Propargyl bromideHCID 3199542-Amino-6-fluorobenzothiazole

Product 1

HCID 22158382HCID 22158382, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
100 °C

Procedure

In 800 ml of n-butanol was dissolved 25.0 g of 2-amino-6-fluorobenzothiazole. With heating at 100° C., 25.0 g of propargyl bromide was dropwise added to the solution. After completion of the dropwise addition, the mixture was heated for 4 hours. The precipitated crystals were taken out by filtration and recrystallized from water to give 26.5 g of 2-imino-6-fluoro-3-propargylbenzothiazole hydrobromide. The hydrobromide, 26.5 g, was added to a mixture of 2.54 g of sodium and 70 ml of ethanol at room temperature followed by refluxing for one hour. After completion of the reaction, the solvent was removed and, water and ethyl acetate were added to the residue followed by separation. After 2N hydrochloric acid was added to the residue obtained from the ethyl acetate phase, water was evaporated to give 20.7 g of 7-fluoro-2-methylimidazo[2,1-b]benzothiazole hydrochloride.

Workup

  1. additionAfter completion of the dropwise addition
  2. temperaturethe mixture was heated for 4 hours
  3. filtrationThe precipitated crystals were taken out by filtration
  4. customrecrystallized from water

Sources & evidence

ORD record
ord-7dd09b02a95540bcaf1b09e0609733f7
Source dataset
uspto-grants-1990_11
Patent number
US04968708

Reaction notes

Loading…