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

HRID 476793Notes

Reaction equation

HRID 476793 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 15702829HCID 15702829, compound

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-5682e26316a2432ba5f25f0d03f2509b
Source dataset
uspto-grants-1989_12
Patent number
US04885363

Reaction notes

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