Ethyl chloroformate → HCID 13117111, compound

HRID 1632838Notes

Reaction equation

HRID 1632838 reaction equation
C(O)(=O)C(O)=O.[F:7][C:8]([F:28])([F:27])[C:9]1[CH:26]=[CH:25][C:12]([O:13][CH:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:17][N:16](C)[CH2:15]2)=[CH:11][CH:10]=1.C([O-])([O-])=O.[K+].[K+].Cl[C:36]([O:38][CH2:39][CH3:40])=[O:37]>C1C=CC=CC=1>[CH2:39]([O:38][C:36]([N:16]1[CH2:15][CH:14]([O:13][C:12]2[CH:25]=[CH:26][C:9]([C:8]([F:7])([F:28])[F:27])=[CH:10][CH:11]=2)[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:17]1)=[O:37])[CH3:40]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 11430Potassium CarbonateHCID 13117096HCID 13117096, compound

Product 1

HCID 13117111HCID 13117111, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a solution of 2-methyl-1,2,3,4-tetrahydro-4-(p-trifluoromethylphenoxy)isoquinoline of Example 4 (18.0 g, 0.06 mole) in 200 ml benzene, is added K2CO3 (20 g, 0.145 mole), and, with stirring, a solution of ethyl chloroformate (7.6 g, 0.07 mole) in 50 ml benzene. After refluxing for four hours, the mixture is cooled, washed twice with 100 ml portions of water, thrice with dilute HCl solution (100 ml), twice with water (100 ml), then dried (saturated NaCl, anhydrous MgSO4). After filtering, the solvent is evaporated to an oil, which solidifies upon cooling, to a solid, 13.7 g (64%), m.p. 84° C. This material is recrystallized from hexanes twice, to yield 11.0 g, m.p. 107°-109° C. of 2-ethoxycarbonyl-1,2,3,4-tetrahydro-4-(p-trifluoromethylphenoxy)isoquinoline.

Workup

  1. temperatureAfter refluxing for four hours
  2. temperaturethe mixture is cooled
  3. washwashed twice with 100 ml portions of water, thrice with dilute HCl solution (100 ml), twice with water (100 ml)
  4. dry with materialdried (saturated NaCl, anhydrous MgSO4)
  5. filtrationAfter filtering
  6. customthe solvent is evaporated to an oil, which
  7. temperatureupon cooling, to a solid, 13.7 g (64%), m.p. 84° C
  8. customThis material is recrystallized from hexanes twice

Sources & evidence

ORD record
ord-354a993457004204be8c00bfaf63458d
Source dataset
uspto-grants-1984_10
Patent number
US04477670

Reaction notes

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