Methylethanimidothioate hydroiodide → HCID 178465573, compound

HRID 2117853Notes

Reaction equation

HRID 2117853 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[N:11]=[C:12]([NH:15][C:16](=[O:18])[CH3:17])[S:13][CH:14]=2)=[CH:4][CH:3]=1.I.[C:20](SC)(=[NH:22])[CH3:21]>CO>[C:20]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[N:11]=[C:12]([NH:15][C:16](=[O:18])[CH3:17])[S:13][CH:14]=2)=[CH:4][CH:3]=1)(=[NH:22])[CH3:21]

Participants

4

Reactant 2

HCID 11680130Methylethanimidothioate hydroiodideHCID 21914814N-{4-[2-(4-aminophenyl)ethyl]thiazol-2-yl}acetamide

Product 1

HCID 178465573HCID 178465573, compoundYield 142.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-(4-(2-(4-Aminophenyl)ethyl)-1,3-thiazol-2-yl)acetamide (100 mg) prepared in a similar manner according to Step 6 of Production Example 1, methyl ethanimidothioate hydriodide (166 mg) and methanol (3 ml) were combined, and refluxed for 1.5 hours. After cooled to room temperature, the mixture was concentrated in vacuo. The residue was purified by flash column chromatography over NH silica gel with chloroform/methanol (20:1→10:1) as an eluent to give N-(4-{2-[4-(ethanimidoylamino)phenyl]ethyl}-1,3-thiazol-2-yl)acetamide (165 mg) as a pale yellow amorphous substance.

Workup

  1. temperaturerefluxed for 1.5 hours
  2. concentrationthe mixture was concentrated in vacuo
  3. customThe residue was purified by flash column chromatography over NH silica gel with chloroform/methanol (20:1→10:1) as an eluent

Sources & evidence

ORD record
ord-84a707cce56446ef8f40fc6a4009eccf
Source dataset
uspto-grants-2008_10
Patent number
US07442715B2

Reaction notes

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