1-Chloroethyl chloroformate → HCID 21699688, compound

HRID 132834Notes

Reaction equation

HRID 132834 reaction equation
Cl.C([N:9]1[CH2:18][CH2:17][C:16]2[N:15]=[C:14]([Cl:19])[C:13]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:12][C:11]=2[CH2:10]1)C1C=CC=CC=1.ClC(OC(Cl)C)=O>ClCCl.CO>[ClH:19].[Cl:19][C:14]1[C:13]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:12][C:11]2[CH2:10][NH:9][CH2:18][CH2:17][C:16]=2[N:15]=1

Participants

5

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 131726930HCID 131726930, compound

Product 1

HCID 21699688HCID 21699688, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

A solution of the product from Step A above (0.095 mg, 0.287 mmol) in 10 mL of dichloromethane was treated with 1-chloroethyl chloroformate (0.050 g; 0.344 mmol), and the mixture was warmed at reflux temperature overnight. The reaction was concentrated under reduced pressure to afford a yellow oil, which was dissolved in 10 mL of methanol. The solution was heated at 40° C. for 2 h, cooled to room temperature and concentrated in vacuo. To the yellow solid was added diisopropyl ether. The pale yellow crystals were collected by filtration and recrystallized from ethanol to afford the title compound. LC/MS: 240.0 (M+1)

Workup

  1. temperaturethe mixture was warmed
  2. temperatureat reflux temperature overnight
  3. concentrationThe reaction was concentrated under reduced pressure
  4. customto afford a yellow oil, which
  5. temperaturecooled to room temperature
  6. concentrationconcentrated in vacuo
  7. additionTo the yellow solid was added diisopropyl ether
  8. filtrationThe pale yellow crystals were collected by filtration
  9. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-5a630813f54146e1a59942a1f740fb6c
Source dataset
uspto-grants-2008_06
Patent number
US07388019B2

Reaction notes

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