3-Nitrophenyl isocyanate → HCID 59020473, compound

HRID 970442Notes

Reaction equation

HRID 970442 reaction equation
[C:1]([NH:8][CH2:9][CH2:10][CH2:11][NH2:12])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[N+:13]([C:16]1[CH:17]=[C:18]([N:22]=[C:23]=[O:24])[CH:19]=[CH:20][CH:21]=1)([O-:15])=[O:14]>CCO>[C:4]([O:3][C:1](=[O:2])[NH:8][CH2:9][CH2:10][CH2:11][NH:12][C:23]([NH:22][C:18]1[CH:19]=[CH:20][CH:21]=[C:16]([N+:13]([O-:15])=[O:14])[CH:17]=1)=[O:24])([CH3:5])([CH3:6])[CH3:7]

Participants

4

Reactant 2

HCID 768353-Nitrophenyl isocyanateHCID 2735700tert-Butyl (3-aminopropyl)carbamate

Product 1

HCID 59020473HCID 59020473, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3.35 g (19.2 mmol) of N-boc-1,3-diaminopropane in 50 ml of EtOH is mixed at 0° C. in portions with 3.15 g (19.2 mmol) of 3-nitrophenyl isocyanate. The batch is stirred overnight at room temperature and then concentrated by evaporation in a rotary evaporator. It is mixed with DCM and washed with water. The organic phase is filtered through a Whatman filter and concentrated by evaporation. 6.4 g (18.9 mmol, corresponding to 98% of theory) of the product is obtained.

Workup

  1. concentrationconcentrated by evaporation in a rotary evaporator
  2. additionIt is mixed with DCM
  3. washwashed with water
  4. filtrationThe organic phase is filtered through a Whatman
  5. filtrationfilter
  6. concentrationconcentrated by evaporation
  7. custom6.4 g (18.9 mmol, corresponding to 98% of theory) of the product is obtained

Sources & evidence

ORD record
ord-e1a49a4168214c7d9149fb3e25adc630
Source dataset
uspto-grants-2007_12
Patent number
US07312225B2

Reaction notes

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