Ethyl chloroformate → HCID 136347865, compound

HRID 1434694Notes

Reaction equation

HRID 1434694 reaction equation
Cl[C:2](OCC)=[O:3].[S:7]1[CH:11]=[CH:10][N:9]=[C:8]1[NH:12][S:13]([C:16]1[CH:34]=[CH:33][C:19]([C:20]([NH:22][NH:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([Cl:32])[CH:26]=2)=[NH:21])=[CH:18][CH:17]=1)(=[O:15])=[O:14]>C1COCC1>[Cl:32][C:27]1[CH:26]=[C:25]([CH:30]=[CH:29][C:28]=1[Cl:31])[CH2:24][N:23]1[C:2](=[O:3])[NH:21][C:20]([C:19]2[CH:18]=[CH:17][C:16]([S:13]([NH:12][C:8]3[S:7][CH:11]=[CH:10][N:9]=3)(=[O:15])=[O:14])=[CH:34][CH:33]=2)=[N:22]1

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 178512758HCID 178512758, compound

Product 1

HCID 136347865HCID 136347865, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
95 °C

Procedure

Ethyl chloroformate (0.05 mL) was added to a solution of 4-(thiazol-2-ylsulfamoyl)-N-(3,4-dichlorobenzylamino)-benzamidine (0.044 mmol) and TEA (0.20 mL) in THF (5 mL) at room temperature and the resulting solution was stirred for 2 h. After concentrating in vacuo 1 N NaOH (4 mL) was added and the solution was heated to 95° C. overnight. After the mixture was cooled to room temperature, the solution was acidified with 1 N HCl and freeze dried. The crude material was purification by reverse phase chromatography to yield 4-[1-(3,4-dichloro-benzyl)-5-oxo-4,5-dihydro-1H-[1,2,4]triazol-3-yl]-N-thiazol-2-yl-benzenesulfonamide (0.002 mmol).

Workup

  1. concentrationAfter concentrating in vacuo 1 N NaOH (4 mL)
  2. additionwas added
  3. temperatureAfter the mixture was cooled to room temperature
  4. customdried
  5. custompurification by reverse phase chromatography

Sources & evidence

ORD record
ord-70281f90a8ed48b5845fdda1b5e9a71e
Source dataset
uspto-grants-2009_11
Patent number
US07615569B2

Reaction notes

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