Benzoyl isothiocyanate → tert-Butyl 3-(3-benzoylthioureido)propylcarbamate

HRID 1755460Notes

Reaction equation

HRID 1755460 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].[C:13]([N:21]=[C:22]=[S:23])(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(Cl)Cl>[C:13]([NH:21][C:22](=[S:23])[NH:1][CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:9])([CH3:11])[CH3:10])(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 2735700tert-Butyl (3-aminopropyl)carbamate

Product 1

HCID 14280415tert-Butyl 3-(3-benzoylthioureido)propylcarbamateYield 99.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice cold solution of tert-butyl 3-aminopropylcarbamate (3.56 g, 20.43 mmol) in CH2Cl2 (80 mL) is added dropwise benzoyl isothiocyanate (3.50 g, 21.45 mmol). The reaction mixture is stirred at room temp for 2 h after which the solvent is removed in vacuo. The resulting residue is partitioned with CH2Cl2 and water, the water layer is extracted with CH2Cl2, the organic layers are combined, washed with brine, dried over Na2SO4, filtered and evaporated to dryness to give 6.89 g (quantitative yield) of the title compound. LC/MS (Condition A): ret. T=3.56 min, (M+H)+ 338.26.

Workup

  1. customis removed in vacuo
  2. customThe resulting residue is partitioned with CH2Cl2 and water
  3. extractionthe water layer is extracted with CH2Cl2
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-ffd6923f2841421ca69313b471b34e95
Source dataset
uspto-grants-2015_10
Patent number
US09169295B2

Reaction notes

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