Dimethylformamide → HCID 86677700, compound

HRID 1499768Notes

Reaction equation

HRID 1499768 reaction equation
N1C(Cl)=NC(Cl)=NC=1[Cl:3].CN(C)C=O.[Cl:15][C:16]1[C:17]([CH3:33])=[C:18]([C:24]([O:30][CH2:31][CH3:32])=[C:25]([CH:27](O)[CH3:28])[CH:26]=1)[C:19]([NH:21][CH2:22][CH3:23])=[O:20]>C(Cl)Cl>[Cl:15][C:16]1[C:17]([CH3:33])=[C:18]([C:24]([O:30][CH2:31][CH3:32])=[C:25]([CH:27]([Cl:3])[CH3:28])[CH:26]=1)[C:19]([NH:21][CH2:22][CH3:23])=[O:20]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 7954Cyanuric chlorideHCID 86677699HCID 86677699, compound

Product 1

HCID 86677700HCID 86677700, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of cyanuric chloride (0.15 g, 0.84 mmol) and N,N-dimethylformamide (0.065 mL, 0.84 mmol) was stirred at room temperature for 10 min and then a solution of 3-chloro-6-ethoxy-N-ethyl-5-(1-hydroxyethyl)-2-methylbenzamide (0.16 g, 0.56 mmol) in methylene chloride (3.1 mL) was added and the reaction was stirred at room temperature overnight. The mixture was diluted with methylene chloride, washed with water, concentrated and purified on silica gel (eluting with 0 to 40% EtOAc in hexanes) to give the desired product (0.13 g, 76%). LCMS calculated for C14H20Cl2NO2 (M+H)+: m/z=304.1; Found: 304.1.

Workup

  1. stirringthe reaction was stirred at room temperature overnight
  2. washwashed with water
  3. concentrationconcentrated
  4. custompurified on silica gel (eluting with 0 to 40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-d30beb063782428bbf27568dbbd18946
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

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