Methylethanimidothioate hydroiodide → HCID 178465573, compound

HRID 1246443Notes

Reaction equation

HRID 1246443 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-4acca64c063844a7939fa4f6fb031bea
Source dataset
uspto-grants-2006_10
Patent number
US07125901B2

Reaction notes

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