2,2,2-Trichloroethyl chloroformate → HCID 66729312, compound

HRID 1098594Notes

Reaction equation

HRID 1098594 reaction equation
[CH:1]([N:4]1[CH:8]=[C:7]([NH2:9])[N:6]=[CH:5]1)([CH3:3])[CH3:2].[C:10](Cl)([O:12][CH2:13][C:14]([Cl:17])([Cl:16])[Cl:15])=[O:11].C([O-])(O)=O.[Na+]>CCOC(C)=O>[CH:1]([N:4]1[CH:8]=[C:7]([NH:9][C:10](=[O:11])[O:12][CH2:13][C:14]([Cl:17])([Cl:16])[Cl:15])[N:6]=[CH:5]1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 870632,2,2-Trichloroethyl chloroformateHCID 516892Sodium BicarbonateHCID 23570471HCID 23570471, compound

Product 1

HCID 66729312HCID 66729312, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirring solution of 1-isopropyl-1H-imidazol-4-amine (0.532 g, 4.25 mmol) in EtOAc (70 ml) was added Troc-Cl (0.614 ml, 4.46 mmol) followed by satd. NaHCO3 (17.23 ml 12.75 mmol). The biphasic mixture was stirred briskly at RT. After 6 h, the layers were separated and the aqueous was extracted with EtOAc (1×). The combined organics were washed with satd. NaHCO3 (1×) and brine (1×), dried, evaporated and triturated (EtOAc/hexanes). The solids were collected by filtration, rinsed with hexanes and dried on the filter to afford 2,2,2-trichloroethyl 1-isopropyl-1H-imidazol-4-ylcarbamate (0.392 g, 31% yield) as a pink-orange solid. 1H NMR (400 MHz, DMSO-d6): δ 10.2 (s, 1H), 7.49 (s, 1H), 7.02 (s, 1H), 4.80 (s, 2H), 4.3-4.25 (m, 1H), 1.35 (d, 6H); MS (ESI) m/z: 300.0 (M+H+), 302.0 (M+2+H+).

Workup

  1. customthe layers were separated
  2. extractionthe aqueous was extracted with EtOAc (1×)
  3. washThe combined organics were washed with satd
  4. dry with materialNaHCO3 (1×) and brine (1×), dried
  5. customevaporated
  6. customtriturated (EtOAc/hexanes)
  7. filtrationThe solids were collected by filtration
  8. washrinsed with hexanes
  9. customdried on the
  10. filtrationfilter

Sources & evidence

ORD record
ord-99b8e8b7b7de4073854220a7a3793e99
Source dataset
uspto-grants-2012_03
Patent number
US08143293B2

Reaction notes

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