1-Bromopropane → HCID 86744380, compound

HRID 1110678Notes

Reaction equation

HRID 1110678 reaction equation
[CH3:1][N:2]([CH3:5])[CH2:3][CH3:4].[Br:6][CH2:7][CH2:8][CH3:9].[Br:10]Br>O>[Br-:6].[Br-:10].[Br-:6].[CH3:1][N+:2]([CH3:5])([CH2:3][CH3:4])[CH2:7][CH2:8][CH3:9].[CH3:1][N+:2]([CH2:7][CH2:8][CH3:9])([CH2:3][CH3:4])[CH3:5].[CH3:1][N+:2]([CH2:7][CH2:8][CH3:9])([CH2:3][CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 78401-BromopropaneHCID 11723Dimethylethylamine2×HCID 24408Bromine

Product 1

HCID 86744380HCID 86744380, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Into a 3-liter flask fitted with a condenser, a 250-ml addition funnel, a thermometer, and a mechanical stirrer were placed N,N-dimethyl-N-ethylamine (256.0 grams, 3.50 moles) and 1000 ml of water. To the stirred solution was added 1-bromopropane (430.5 grams, 3.50 mole) and the two-phase mixture heated to 50° C. with vigorous agitation. After 8.5 hours the 1H--NMR nuclear magnetic resonance spectrum of the upper layer indicated that the N,N-dimethyl-N-ethylamine had been completely consumed. The amber solution was cooled to room temperature, and bromine (560 grams, 3.50 moles) was added dropwise over a period of 1.5 hour with vigorous stirring. The tribromide separated as a dark red lower layer. The layers were separated and the residual water (appx. 25 grams) removed from the tribromide layer by distillation at 50° C. under reduced pressure. The yield of dark red N,N-dimethyl-N-ethyl-N-propylammonium tribromide was 1083.0 grams (87% from N,N-dimethyl-N-ethylamine). Analysis: %Brtot =68.73% (exp), 67.35% (theo): %Brox =47.58 % (exp), 44.90% (theo).

Workup

  1. customInto a 3-liter flask fitted with a condenser, a 250-ml addition funnel
  2. customhad been completely consumed
  3. temperatureThe amber solution was cooled to room temperature
  4. customThe tribromide separated as a dark red lower layer
  5. customThe layers were separated
  6. customthe residual water (appx. 25 grams) removed from the tribromide layer by distillation at 50° C. under reduced pressure

Sources & evidence

ORD record
ord-ee9b1231d3374a70b343700c6829475c
Source dataset
uspto-grants-1990_12
Patent number
US04976874

Reaction notes

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