1-Chloroethyl chloroformate → HCID 18186940, compound

HRID 1296644Notes

Reaction equation

HRID 1296644 reaction equation
ClC(OC(Cl)C)=O.C([N:15]1[CH2:20][CH2:19][N:18]([C:21]2[CH:26]=[N:25][CH:24]=[C:23]([Cl:27])[N:22]=2)[CH:17]([CH2:28][CH3:29])[CH2:16]1)C1C=CC=CC=1>ClCCl>[Cl:27][C:23]1[N:22]=[C:21]([N:18]2[CH2:19][CH2:20][NH:15][CH2:16][CH:17]2[CH2:28][CH3:29])[CH:26]=[N:25][CH:24]=1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 18186916HCID 18186916, compound

Product 1

HCID 18186940HCID 18186940, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Choroethyl chloroformate (4.16 g, 29.1 mmol) was added dropwise under 2 h to a stirred solution of the product obtained in step 2 above (6.15 g, 19.4 mmol) in dry dichloromethane (75 mL) at 0° C. After being stirred at room temperature for 15 h, the reaction mixture was concentrated in vacuo and methanol was added. The mixture was heated at reflux for 2 h and concentrated. The residue was dissolved in CHCl3 and passed through a short (4 cm) plug of silica gel using CHCl3/MeOH (8:2) as eluent. Solvents were evaporated off and the residue was purified by chromatography on silica gel (12×5 cm) using CHCl3/MeOH/Et3N (95:5:0.2) as eluent. This provided 1.9 g (43%) of the title compound as an oil. MS m/z 226/228 (M)+ (35Cl/37Cl-isotope pattern). HRMS m/z calcd for C10H15ClN4 (M)+ 226.0985, found 226.0986.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo and methanol
  2. additionwas added
  3. temperatureThe mixture was heated
  4. temperatureat reflux for 2 h
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in CHCl3
  7. customSolvents were evaporated off
  8. customthe residue was purified by chromatography on silica gel (12×5 cm)

Sources & evidence

ORD record
ord-4dda254a9a9740b097a72b73f7af073f
Source dataset
uspto-grants-2007_07
Patent number
US07247633B2

Reaction notes

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