Phosgene → Methyl(pentyl)carbamyl chloride

HRID 66338

Reaction equation

HRID 66338 reaction equation
C(N(CC)CC)C.[C:8]([Cl:11])(Cl)=[O:9].[CH3:12][NH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]>CC1CCCCC1.C1(C)C=CC=CC=1>[CH3:12][N:13]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:8]([Cl:11])=[O:9]

Participants

6

Reactant 3

HCID 6371PhosgeneHCID 8471TriethylamineHCID 117479N-Methylpentylamine

Product 1

HCID 15209943Methyl(pentyl)carbamyl chloride

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 7962MethylcyclohexaneSolvent

Conditions

Temperature
-10 °C

Procedure

Triethylamine (14 cc.) is added over the course of 8 minutes to a 2.5N solution (42 cc.) of phosgene in methylcyclohexane, cooled to -10° C., and a solution of N-methylpentylamine (13.7 cc.) in toluene (50 cc.) is then added whilst maintaining the temperature at -10° C. The mixture is stirred for 1 hour at +5° C. The insoluble material is then filtered off and washed with toluene (80 cc.). The organic solutions are dried over calcium chloride (10 g.). After filtration, the solvents are evaporated under reduced pressure (40 mm.Hg). The residue is distilled under reduced pressure to give N-methyl-N-pentylcarbamoyl chloride (5.6 g.), b.p. 120-125° C./40 mm.Hg.

Workup

  1. temperaturewhilst maintaining the temperature at -10° C
  2. filtrationThe insoluble material is then filtered off
  3. washwashed with toluene (80 cc.)
  4. dry with materialThe organic solutions are dried over calcium chloride (10 g.)
  5. filtrationAfter filtration
  6. customthe solvents are evaporated under reduced pressure (40 mm.Hg)
  7. distillationThe residue is distilled under reduced pressure

Sources & evidence

ORD record
ord-a885dadfe7b7440faa0f634571ffd442
Source dataset
uspto-grants-1978_12
Patent number
US04131674

Linked notes

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