1-Chloroethyl chloroformate → HCID 68468807, compound

HRID 2237437Notes

Reaction equation

HRID 2237437 reaction equation
C([N:8]1[CH2:14][CH2:13][C:12]2[C:15]([Cl:19])=[C:16]([Cl:18])[S:17][C:11]=2[CH2:10][CH2:9]1)C1C=CC=CC=1.ClC(OC(Cl)C)=O>ClC(Cl)C.C(Cl)Cl.CO>[ClH:18].[Cl:18][C:16]1[S:17][C:11]2[CH2:10][CH2:9][NH:8][CH2:14][CH2:13][C:12]=2[C:15]=1[Cl:19]

Participants

6

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 58256121HCID 58256121, compound

Product 1

HCID 68468807HCID 68468807, compoundYield 54%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
22 °C

Procedure

A solution of the product from step g) (727 mg, 2.33 mmol) in anhydrous dichloroethane (11.6 ml) was cooled to 0° C., treated with 1-Chloroethyl chloroformate (1.27 ml, 11.65 mmol) and the reaction was warmed to 22° C. for 1 hour. The reaction diluted with CH2Cl2 (50 ml) and washed with sat. NaHCO3 (25 ml). The sat. NaHCO3 was back extracted with CH2Cl2 and the combined organic layers were washed with brine (25 ml), dried (MgSO4) and concentrated providing an oily residue, which was taken up in anhydrous MeOH (75 ml) and refluxed for 1 hour. The MeOH was evaporated and the crude residue was triturated with ether and filtered providing 323 mg (54%) of the subtitle compound. 1H NMR (300 MHz, DMSO) δ 9.60 (br s, 2H); 3.14-3.28 (m, 6H); 2.97-3.50 (m, 2H); MS: ESI (positive): 222, 224 (M+H).

Workup

  1. washwashed with sat. NaHCO3 (25 ml)
  2. extractionThe sat. NaHCO3 was back extracted with CH2Cl2
  3. washthe combined organic layers were washed with brine (25 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customproviding an oily residue, which
  7. temperaturerefluxed for 1 hour
  8. customThe MeOH was evaporated
  9. customthe crude residue was triturated with ether
  10. filtrationfiltered

Sources & evidence

ORD record
ord-47fed3f43d0c4826bf0d86082a9fe136
Source dataset
uspto-grants-2010_05
Patent number
US07718647B2

Reaction notes

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