Diisopropylamine → 2-Cyanoethyl N,N-diisopropylchlorophosphoramidite

HRID 1494503Notes

Reaction equation

HRID 1494503 reaction equation
[CH:1]([NH:4][CH:5]([CH3:7])[CH3:6])([CH3:3])[CH3:2].[C:8]([CH2:10][CH2:11][O:12][P:13](Cl)[Cl:14])#[N:9]>C(OCC)C>[C:8]([CH2:10][CH2:11][O:12][P:13]([Cl:14])[N:4]([CH:5]([CH3:7])[CH3:6])[CH:1]([CH3:3])[CH3:2])#[N:9]

Participants

4

Reactant 2

HCID 7912DiisopropylamineHCID 195897Phosphorodichloridous acid, 2-cyanoethyl ester

Product 1

HCID 27348442-Cyanoethyl N,N-diisopropylchlorophosphoramidite

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Diisopropylamine (156 millimoles) was dissolved in 80 ml of diethyl ether, and then 34.7 millimoles of beta-cyanoethoxydichlorophosphine was added. The mixture was stirred at room temperature for 12 hours. After the reaction, the resulting diisopropyl ammonium chloride was separated by filtration. The ether solution was distilled to give beta-cyanoethoxymonochloro(N,N-diisopropylamino) phosphine as an oil. The yield was 73 mole%, and the product had a boiling point of 102 to 104° C. (0.08 mmHg).

Workup

  1. customAfter the reaction
  2. customthe resulting diisopropyl ammonium chloride was separated by filtration
  3. distillationThe ether solution was distilled

Sources & evidence

ORD record
ord-174387a7097b43549d2d321ec19f15e6
Source dataset
uspto-grants-1991_06
Patent number
US05026838

Reaction notes

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