Phosgene → Dipentylcarbamyl chloride

HRID 486743

Reaction equation

HRID 486743 reaction equation
[CH2:1]([NH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[CH2:2][CH2:3][CH2:4][CH3:5].[OH-].[Na+].[C:14](Cl)([Cl:16])=[O:15]>C1(C)C=CC=CC=1>[CH2:7]([N:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[C:14]([Cl:16])=[O:15])[CH2:8][CH2:9][CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 14798Sodium HydroxideHCID 16316Dipentylamine

Product 1

HCID 22106956Dipentylcarbamyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A mixture of 7.86 g. (50.0 mmole) of dipentylamine, 18.05 ml (50.0 mmole) of 2.77M NaOH solution and 60 ml of toluene was vigorously stirred at -7° to -5° C., and 60 ml (115.8 mmole) of 1.93M phosgene in toluene was added dropwise over 1 hour. After stirring an additional 30 min., the cold mixture was separated and the toluene layer was dried over solid NaCl. After filtering, nitrogen was bubbled through the solution for 1 hour and the solution was concentrated in vacuo to 10.5 g. (95%) of light yellow oil.

Workup

  1. additionA mixture of 7.86 g
  2. customthe cold mixture was separated
  3. dry with materialthe toluene layer was dried over solid NaCl
  4. filtrationAfter filtering
  5. customnitrogen was bubbled through the solution for 1 hour
  6. concentrationthe solution was concentrated in vacuo to 10.5 g

Sources & evidence

ORD record
ord-d74560f12b2d4b0fa6aace40dd0c3144
Source dataset
uspto-grants-1994_03
Patent number
US05292726

Linked notes

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