Diisopropylethylamine → HCID 22174357, compound

HRID 1796894Notes

Reaction equation

HRID 1796894 reaction equation
Br[CH2:2][C:3]([NH:5][C:6]1[C:11]([CH3:12])=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:13])=[O:4].Br.[CH3:15][S:16](=[S:22])([O:18]CCN)=[O:17].[CH:23]([N:26](C(C)C)CC)(C)[CH3:24]>CN(C=O)C>[CH3:13][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]([CH3:12])[C:6]=1[NH:5][C:3](=[O:4])[CH2:2][NH:26][CH2:23][CH2:24][S:18][S:16](=[O:17])(=[O:22])[CH3:15]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27634872-bromo-N-(2,6-dimethylphenyl)acetamideHCID 53443081HCID 53443081, compound

Product 1

HCID 22174357HCID 22174357, compoundYield 63.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-bromo-N-(2,6-dimethylphenyl)acetamide (2 g; 8.26 mmol), aminoethyl methanethiosulfonate hydrobromide (2.8 g; 11.86 mmol), and diisopropylethylamine (4 mL; 23 mmol) in dry DMF (70 mL) was stirred at room temperature for 3.5 hours. The solution was evaporated and the residue purified by column chromatography on SiO2. The column was eluted with CH2Cl2/MeOH/NH4OH 95:5:0.2 and evaporation of the fractions containing the desired product afforded a pale yellow oil (1.66 g) which crystallized upon standing in the freezer. This was disolved in methanol/ether (1:1; 50 mL). A saturated solution of HCl in ether (4 mL) was added. The precipitated hydrochloride salt was filtered and dried to yield a light brown solid (1.15 g; 39% yield) with a melting point of 158-162° C. 1H NMR (500 MHz,(CD3)2SO) δ 9.93 (s, 1H), 9.32 (s, br, 2H), 7.10-7.07 (m, 3H); 4.08 (s, 2H), 3.61 (s, 3H), 3.54 (t, J=7.2 Hz, 2H), 3.40 (t, J7.2 Hz, 2H), 2.16 (s, 6H).

Workup

  1. customThe solution was evaporated
  2. customthe residue purified by column chromatography on SiO2
  3. washThe column was eluted with CH2Cl2/MeOH/NH4OH 95:5:0.2 and evaporation of the fractions
  4. additioncontaining the desired product

Sources & evidence

ORD record
ord-d6c068991dc2467ea4fee07507c33ca5
Source dataset
uspto-grants-2006_04
Patent number
US07033765B1

Reaction notes

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