Benzoyl isothiocyanate → HCID 86597776, compound

HRID 2249601Notes

Reaction equation

HRID 2249601 reaction equation
[C:1]([O:5][C:6](=[O:13])[NH:7][C:8]([CH3:12])([CH3:11])[CH2:9][NH2:10])([CH3:4])([CH3:3])[CH3:2].[C:14]([N:22]=[C:23]=[S:24])(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1COCC1>[C:1]([O:5][C:6](=[O:13])[NH:7][C:8]([CH3:12])([CH3:11])[CH2:9][NH:10][C:23]([NH:22][C:14](=[O:21])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[S:24])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 45072480tert-Butyl (1-amino-2-methylpropan-2-yl)carbamate

Product 1

HCID 86597776HCID 86597776, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (2-amino-1,1-dimethyl-ethyl)-carbamic acid tert-butyl ester [CAS 320581-09-7] (43.9 g) and benzoyl isothiocyanate (31.8 ml) in THF (400 ml) was stirred at 60° C. overnight. The mixture was concentrated. Small amounts of toluene were added. Insoluble parts were filtered off and the remaining solution was concentrated. The residue was disolved in ethyl acetate and extracted with brine. The organic layer was dried (MgSO4) and evaporated. Crystallisation of the obtained residue in toluene and hexane provided 53.0 g of white crystals.

Workup

  1. concentrationThe mixture was concentrated
  2. additionSmall amounts of toluene were added
  3. filtrationInsoluble parts were filtered off
  4. concentrationthe remaining solution was concentrated
  5. extractionextracted with brine
  6. dry with materialThe organic layer was dried (MgSO4)
  7. customevaporated
  8. customCrystallisation of the obtained residue in toluene

Sources & evidence

ORD record
ord-39ff3a85e1bc43f2b31c639bfd799c4f
Source dataset
uspto-grants-2008_01
Patent number
US07314884B2

Reaction notes

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