tert-Butyl isothiocyanate → HCID 86584348, compound

HRID 2229849Notes

Reaction equation

HRID 2229849 reaction equation
[NH2:1][C@H:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:3][OH:4].[C:11]([N:15]=[C:16]=[S:17])([CH3:14])([CH3:13])[CH3:12]>C(O)C.C(OCC)(=O)C>[C:11]([NH:15][C:16]([NH:1][C@H:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:3][OH:4])=[S:17])([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 2

HCID 11544tert-Butyl isothiocyanateHCID 2724025(R)-beta-aminophenethyl alcohol

Product 1

HCID 86584348HCID 86584348, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-(tert-Butyl)-N′-[(1R)-2-hydroxy-1-phenylethyllthiourea: The process is performed under the conditions of Example 1, starting with 2.74 g of (R)-(−)-2-amino-2-phenylethanol and 2.8 cm3 of tert-butyl isothiocyanate in 15 cm3 of ethanol for 20 hours at a temperature in the region of 20° C. The reaction medium is concentrated under reduced pressure (5 kPa) at a temperature in the region of 50° C. A yellow oil is obtained, which is dissolved in 100 cm3 of ethyl acetate and the organic solution is then washed with twice 50 cm3 of aqueous sodium hydrogen carbonate solution and twice with aqueous sodium chloride solution. After drying over sodium sulfate, the organic solution is filtered and then concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C. 4.9 g of N-(tert-butyl)-N′-[(1R)-2-hydroxy-1-phenylethyl]thiourea are obtained in the form of a yellow solid melting at 98° C.

Workup

  1. concentrationThe reaction medium is concentrated under reduced pressure (5 kPa) at a temperature in the region of 50° C
  2. customA yellow oil is obtained
  3. washthe organic solution is then washed with twice 50 cm3 of aqueous sodium hydrogen carbonate solution and twice with aqueous sodium chloride solution
  4. dry with materialAfter drying over sodium sulfate
  5. filtrationthe organic solution is filtered
  6. concentrationconcentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C

Sources & evidence

ORD record
ord-824a765d4fb14b978db1846ca2634f5c
Source dataset
uspto-grants-2002_07
Patent number
US06420566B2

Reaction notes

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