N-Boc thiourea → HCID 45117850, compound

HRID 32849Notes

Reaction equation

HRID 32849 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]([NH2:11])=[S:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:12]([S:14][C:15](=O)[CH2:16]Br)[CH3:13]>C(O)C>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]1[S:10][CH:13]=[C:12]([S:14][CH2:15][CH3:16])[N:11]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 4095660N-Boc thioureaHCID 12350683S-Ethyl bromoethanethioate

Product 1

HCID 45117850HCID 45117850, compoundYield 58.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

N-tert-butoxycarbonyl-thiourea (0.600 g, 3.40 mmole) was suspended in ethanol (5 mL) and the mixture was cooled in an ice-water bath. To this mixture was added a solution of bromo-thioacetic acid S-ethyl ester (0.880 g [75% pure]; 3.61 mmole) in ethanol (5 mL). Following completion of the addition, the mixture was warmed to room temperature and stirred overnight. After 20 hours, the reaction was concentrated. The residue was partitioned between methylene chloride and water. The organic phase was washed with water and brine. The aqueous phases were then backwashed with methylene chloride. The two organic phases were combined, dried over sodium sulfate and concentrated. The crude material was purified by chromatography over silica gel eluted with 20% v/v ethyl acetate in hexanes, to give (4-ethylsulfanyl-thiazol-2yl)-carbamic acid tert-butyl ester (0.514 g, 58%).

Workup

  1. temperaturethe mixture was cooled in an ice-water bath
  2. additioncompletion of the addition
  3. waitAfter 20 hours
  4. concentrationthe reaction was concentrated
  5. customThe residue was partitioned between methylene chloride and water
  6. washThe organic phase was washed with water and brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customThe crude material was purified by chromatography over silica gel
  10. washeluted with 20% v/v ethyl acetate in hexanes

Sources & evidence

ORD record
ord-a58c5cbf4c0c47f5be3e7f5aa1a812f9
Source dataset
uspto-grants-2008_09
Patent number
US07427635B2

Reaction notes

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