Ammonia → N-(1-methyl-1-(3-thioureidophenyl)ethyl)carbamic acid t-butyl ester

HRID 1861897Notes

Reaction equation

HRID 1861897 reaction equation
[C:1](Cl)(Cl)=[S:2].[C:5]([O:9][C:10](=[O:22])[NH:11][C:12]([CH3:21])([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([NH2:20])[CH:15]=1)[CH3:13])([CH3:8])([CH3:7])[CH3:6].C(=O)([O-])[O-].[Ca+2].[NH3:28]>C(Cl)Cl.O>[C:5]([O:9][C:10](=[O:22])[NH:11][C:12]([CH3:13])([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([NH:20][C:1]([NH2:28])=[S:2])[CH:15]=1)[CH3:21])([CH3:6])([CH3:7])[CH3:8]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 10040ThiophosgeneHCID 10112Calcium CarbonateHCID 229810903-[2-(Boc-amino)-2-propyl]aniline

Product 1

HCID 22981132N-(1-methyl-1-(3-thioureidophenyl)ethyl)carbamic acid t-butyl esterYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Thiophosgene (0.12 ml) and a solution of the compound (284 mg) obtained in Example 2 in methylene chloride (10 ml) were added dropwise to a suspension of calcium carbonate (319 mg) in water (5 ml) at room temperature and stirred at room temperature for 5 h; thereafter, a 28% aqueous ammonia solution (5 ml) was added to the reaction mixture and stirred at room temperature for 16 h. After neutralization with 2 N HCl, the reaction mixture was extracted with ethyl acetate and the organic layer was washed with a saturated aqueous sodium chloride solution, dried with anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=6:4) to yield 351 mg of the titled compound (yield, 89%).

Workup

  1. stirringstirred at room temperature for 16 h
  2. extractionAfter neutralization with 2 N HCl, the reaction mixture was extracted with ethyl acetate
  3. washthe organic layer was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried with anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=6:4)

Sources & evidence

ORD record
ord-39e09d5a2fc84f0baf78893282d6b565
Source dataset
uspto-grants-2003_03
Patent number
US06534546B1

Reaction notes

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