HCID 87332147, compound → HCID 71561786, compound

HRID 2174727Notes

Reaction equation

HRID 2174727 reaction equation
[CH3:1][N:2]([CH3:15])/[CH:3]=[CH:4]/[C:5]([C:7]1[S:11][C:10]([NH:12][CH3:13])=[N:9][C:8]=1[CH3:14])=[O:6].[Cl:16]N1C(=O)CCC1=O.CO>>[Cl:16]/[C:4](=[CH:3]\[N:2]([CH3:1])[CH3:15])/[C:5]([C:7]1[S:11][C:10]([NH:12][CH3:13])=[N:9][C:8]=1[CH3:14])=[O:6]

Participants

3

Reactant 2

HCID 87332147HCID 87332147, compoundHCID 118007580HCID 118007580, compound

Product 1

HCID 71561786HCID 71561786, compoundYield 43%

Procedure

To a well stirred solution of (E)-3-(dimethylamino)-1-(4-methyl-2-(methylamino)thiazol-5-yl) prop-2-en-1-one (2 mmol) in 50 ml methanol N-chlorosuccinimide (2.5 mmol) was added. The reaction mixture was stirred for 30 minutes. The mixture was evaporated to dryness and the residue was purified by column chromatography using EtoAc to yield (Z)-2-chloro-3-(dimethylamino)-1-(4-methyl-2-(methylamino)thiazol-5-yl)prop-2-en-1-one as light yellow solid (43%). 1H-NMR (DMSO-d6) δ: 2.37 (s, 3H, CH3), 2.98 (s, 3H, CH3), 3.25 (s, 6H, 2×CH3), 6.43 (s, 1H, NH), 7.42 (s, 1H, CH). HR-MS (m/z): calcd for C10H14ClN3OS, 259.0546; found 260.0541 [M+H]+.

Workup

  1. customThe mixture was evaporated to dryness
  2. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-8d3c235e9e1f4bcba39e282ebda08c10
Source dataset
uspto-grants-2015_06
Patent number
US09062039B2

Reaction notes

Loading…