Phosgene → Methyl(pentyl)carbamyl chloride
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
Product 1
Reagents, catalysts & solvents 2
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
- temperaturewhilst maintaining the temperature at -10° C
- filtrationThe insoluble material is then filtered off
- washwashed with toluene (80 cc.)
- dry with materialThe organic solutions are dried over calcium chloride (10 g.)
- filtrationAfter filtration
- customthe solvents are evaporated under reduced pressure (40 mm.Hg)
- distillationThe residue is distilled under reduced pressure
Sources & evidence
- ORD record
- ord-657c6a6f94ab4df7832c90afb19a3f64
- Source dataset
- uspto-grants-1978_04
- Patent number
- US04086348
Reaction notes
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