Diethylenetriamine → HCID 19032072, compound

HRID 266018Notes

Reaction equation

HRID 266018 reaction equation
Br[CH:2]([CH2:10][O:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1)[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[NH2:22][CH2:23][CH2:24][NH:25][CH2:26][CH2:27][NH2:28]>C(#N)C>[C:6]([O:5][C:3](=[O:4])[CH:2]([CH2:10][O:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1)[NH:22][CH2:23][CH2:24][NH:25][CH2:26][CH2:27][NH2:28])([CH3:9])([CH3:8])[CH3:7]

Participants

4

Reactant 2

HCID 8111DiethylenetriamineHCID 14959737HCID 14959737, compound

Product 1

HCID 19032072HCID 19032072, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
35 °C

Procedure

A solution of 14 g of t-butyl 2-bromo-3-[(4-nitrophenyl)methoxy]propanoate (prepared according to the procedure described by P. L. Rings et al., Synth. Commun., 1993, 23, 2639) (0.0389 mol), in 30 ml of acetonitrile was added to a solution of 20 g of diethylenetriamine (0.19 mol) in 20 ml of acetonitrile kept at 0°-5° C. and under inert atmosphere. The solution was then heated to 35° C. for 4 h. The solvent was evaporated under vacuum and 100 ml of a NaCl saturated solution were added to the residue. The solution was extracted with Et2O; the organic phase was washed with H2O, dried and concentrated under vacuum to obtain 12 g of the desired product (0.031 mol).

Workup

  1. customkept at 0°-5° C. and under inert atmosphere
  2. customThe solvent was evaporated under vacuum and 100 ml of a NaCl saturated solution
  3. additionwere added to the residue
  4. extractionThe solution was extracted with Et2O
  5. washthe organic phase was washed with H2O
  6. customdried
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-d1589c4b1bf041258ccd1956cc00bd42
Source dataset
uspto-grants-1997_07
Patent number
US05649537

Reaction notes

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