Ammonia → HCID 21915108, compound

HRID 2117924Notes

Reaction equation

HRID 2117924 reaction equation
[ClH:1].[C:2]([NH:5][C:6]1[S:7][CH:8]=[C:9]([CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][C:20](=[NH:23])OC)=[CH:15][CH:14]=2)[N:10]=1)(=[O:4])[CH3:3].[Cl-].[NH4+:25].N>CCO.CO>[ClH:1].[NH2:25][C:20](=[NH:23])[CH2:19][C:16]1[CH:17]=[CH:18][C:13]([CH2:12][CH2:11][C:9]2[N:10]=[C:6]([NH:5][C:2](=[O:4])[CH3:3])[S:7][CH:8]=2)=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 21915039HCID 21915039, compound

Product 1

HCID 21915108HCID 21915108, compoundYield 58.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

Methyl 2-(4-{2-[2-(acetylamino)-1,3-thiazol-4-yl]ethyl}phenyl)ethanimidoate hydrochloride (600 mg) was dissolved in EtOH (12 ml). Then ammonium chloride (136 mg) and ammonia in methanol (2 ml) were added to the solution. The reaction mixture was refluxed for 4 hours under N2 atmosphere. After cooled to r.t., the suspension was filtered in vacuo. The filtrate was concentrated in vacuo, and the residue was solidified with EtOH/diethyl ether to give N-(4-{2-[4-(2-amino-2-iminoethyl)phenyl]ethyl}-1,3-thiazol-2-yl)acetamide hydrochloride (338.6 mg) as an off-white solid.

Workup

  1. temperatureThe reaction mixture was refluxed for 4 hours under N2 atmosphere
  2. filtrationthe suspension was filtered in vacuo
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-368d7534fdfe40ad89d80c2e7c2c62bf
Source dataset
uspto-grants-2008_10
Patent number
US07442715B2

Reaction notes

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