Dimethyl Sulfide → 1-Benzyl-1,4,7,10-tetraazacyclododecane

HRID 1456888Notes

Reaction equation

HRID 1456888 reaction equation
[CH2:1]([N:8]1[CH2:19][C:18](=O)[NH:17][CH2:16][CH2:15][NH:14][CH2:13][CH2:12][NH:11][C:10](=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CSC>O1CCCC1>[CH2:1]([N:8]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15][NH:14][CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 1068Dimethyl SulfideHCID 157028294-Benzyl-1,4,7,10-tetraazacyclododecane-2,6-dione

Product 1

HCID 100840821-Benzyl-1,4,7,10-tetraazacyclododecane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 890 mg (3.07 mmol) of 1-benzyl-3,11-dioxo-1,4,7,10-tetraazacyclododecane in tetrahydrofuran under nitrogen was added 2.64 ml of 8M borane-methyl sulfide complex (21.1 mol, 7 equivalents). The mixture was heated to reflux allowing the methyl sulfide to distill out of the reaction flask. After 2 hours, the reaction was quenched by the addition of 12 ml 1.8M hydrochloric acid in methanol and refluxed for an additional 3 hours. Volatiles were removed by evaporation, and the solid resuspended in methanol and reevaporated. The product was crystallized from methanol/ethyl acetate; yield 455 mg, 37%. Mass spectrum (CI): m/e 263 (M+H).

Workup

  1. additionwas added 2.64 ml of 8M borane-methyl sulfide complex (21.1 mol, 7 equivalents)
  2. temperatureThe mixture was heated
  3. temperatureto reflux
  4. distillationto distill out of the reaction flask
  5. customthe reaction was quenched by the addition of 12 ml 1.8M hydrochloric acid in methanol
  6. temperaturerefluxed for an additional 3 hours
  7. customVolatiles were removed by evaporation
  8. customreevaporated
  9. customThe product was crystallized from methanol/ethyl acetate

Sources & evidence

ORD record
ord-8e0dd062332042778c9c931619c142d1
Source dataset
uspto-grants-1998_12
Patent number
US05846519

Reaction notes

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