Dichloromethane → 3-(4-Cyanophenyl)-2,3-dihydro-imidazo[2,1-b]thiazole-5-carboxylic acid hydrochloride

HRID 844259Notes

Reaction equation

HRID 844259 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:13][S:12][C:11]3=[N:14][CH:15]=[C:16]([C:17]([O:19]CC)=[O:18])[N:10]23)=[CH:5][CH:4]=1)#[N:2].C(Cl)[Cl:23].[OH-].[Na+]>C(O)C>[ClH:23].[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:13][S:12][C:11]3=[N:14][CH:15]=[C:16]([C:17]([OH:19])=[O:18])[N:10]23)=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 22612521Ethyl 3-(4-cyanophenyl)-2,3-dihydro-imidazo[2,1-b]thiazole-5-carboxylate

Product 1

HCID 699341033-(4-Cyanophenyl)-2,3-dihydro-imidazo[2,1-b]thiazole-5-carboxylic acid hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the ester from Step C (4.81 g, 16.1 mmol) in ethanol (10 mL)/methylene chloride (10 mL) at 0° C. was added sodium hydroxide (10 M in water, 2.09 mL, 20.9 mmol). After stirring for 16 hours, the organic solvents were evaporated in vacuo at 25° C., and the water removed by a stream of nitrogen. The crude product was acidified by the addition of hydrogen chloride (1 M in diethylether, 40 mL) and reconcentrated to provide the crude product as a white solid which was sufficiently pure for use in the next step.

Workup

  1. customthe organic solvents were evaporated in vacuo at 25° C.
  2. customthe water removed by a stream of nitrogen
  3. additionThe crude product was acidified by the addition of hydrogen chloride (1 M in diethylether, 40 mL)

Sources & evidence

ORD record
ord-5f85a464c4e944c5911079b13f266bc1
Source dataset
uspto-grants-2002_04
Patent number
US06380228B1

Reaction notes

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