1-Chloroethyl chloroformate → HCID 59625895, compound

HRID 2365281Notes

Reaction equation

HRID 2365281 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([CH:17]2[CH2:20][N:19](C(C3C=CC=CC=3)C3C=CC=CC=3)[CH2:18]2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC(OC(Cl)C)=O>C(Cl)Cl>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][N:14]([CH:17]2[CH2:18][NH:19][CH2:20]2)[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 59625794HCID 59625794, compound

Product 1

HCID 59625895HCID 59625895, compoundYield 125%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 8b (3.4 g, 7.7 mmol) in CH2Cl2 was added 1-chloroethyl chloroformate (2.5 mL, 23.1 mmol) at 0° C. under a N2 atmosphere. The ice bath was removed and the reaction stirred for 2 h. The organic phase was concentrated under reduced pressure, and MeOH was added to the resultant residue. The reaction was refluxed for 2 h at which time the solvent was removed under reduced pressure. The residue was partitioned between chloroform and aqueous HCl (1N). The aqueous layer was separated, made basic with aqueous NaOH (3N), and extracted with chloroform. The organic layer was then dried (K2CO3), filtered and concentrated to afford compound 8c (2.65 g). MS m/z (M+H+) 276.

Workup

  1. customThe ice bath was removed
  2. concentrationThe organic phase was concentrated under reduced pressure, and MeOH
  3. additionwas added to the resultant residue
  4. temperatureThe reaction was refluxed for 2 h at which time the solvent
  5. customwas removed under reduced pressure
  6. customThe residue was partitioned between chloroform and aqueous HCl (1N)
  7. customThe aqueous layer was separated
  8. extractionextracted with chloroform
  9. dry with materialThe organic layer was then dried (K2CO3)
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-b7698b7abc054e31b090f44bb34da263
Source dataset
uspto-grants-2014_04
Patent number
US08697684B2

Reaction notes

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