Carbon Disulfide → HCID 59367272, compound

HRID 1923984Notes

Reaction equation

HRID 1923984 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5](=[O:14])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:15](=[S:17])=S>C(O)C>[CH2:7]([O:6][C:5]([NH:4][CH2:3][CH2:2][NH:1][C:15]([NH:1][CH2:2][CH2:3][NH:4][C:5](=[O:14])[O:6][CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)=[S:17])=[O:14])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 6348Carbon DisulfideHCID 2794257Benzyl N-(2-aminoethyl)carbamate

Product 1

HCID 59367272HCID 59367272, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of benzyl 2-aminoethylcarbamate LIX (3 g; 15.45 mmol) in anhydrous ethanol (20 mL) was added carbon disulfide (0.47 mL; 7.73 mmol). The mixture was heated under gently reflux for 22 h. After cooling to r.t., the product precipitated and was filtered, washed with anhydrous ethanol (3×) and air dried. Benzyl N-(2-{[(2-{[(benzyloxy)carbonyl]amino}ethyl)carbamothioyl]amino}ethyl)carbamate LX was obtained as white solid (2.97 g; 6.90 mmol; 89.3% yield). 1H NMR (DMSO-d6) 3.10-3.14 (m, 4H), 3.37-3.42 (m, 4H), 5.00 (s, 4H), 7.30-7.37 (m, 12H), 7.54 (brs, 2H); ESIMS found for C21H26N4O4S m/z 431.4 (M+H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder gently reflux for 22 h
  3. customthe product precipitated
  4. filtrationwas filtered
  5. washwashed with anhydrous ethanol (3×) and air
  6. customdried

Sources & evidence

ORD record
ord-0c897b4037a24c7cba3989e1a8142de4
Source dataset
uspto-grants-2012_05
Patent number
US08178490B2

Reaction notes

Loading…