1-Bromo-3-chloropropane → HCID 21438254, compound

HRID 2397444Notes

Reaction equation

HRID 2397444 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[S:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[NH:5][C:4]=2[CH:3]=1.C([Li])CCC.Br[CH2:22][CH2:23][CH2:24][Cl:25]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[S:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]([CH2:22][CH2:23][CH2:24][Cl:25])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 131063502-Bromo-10H-phenothiazineHCID 178418339Butyllithium

Product 1

HCID 21438254HCID 21438254, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

A solution of 2-bromophenothiazine (41.72 g., 0.05 mole) in 200 ml. of dry toluene was added to a stirred solution of 9.6 g. (0.15 mole) of n-butyllithium in 100 ml. of dry toluene. The stirred solution was warmed for about 2.0 hours at 45°-50° C. and then 31.5 g. (0.20 mole) of bromopropylchloride in 50 ml. of dry toluene was added. The mixture was refluxed for 15 hours. The cooled reaction mixture was washed with water, dried over sodium sulfate and the dried solution concentrated at reduced pressure. The residual oil was distilled to give the product, 2-bromo-10-(3-chloropropyl)phenothiazine.

Workup

  1. temperatureThe stirred solution was warmed for about 2.0 hours at 45°-50° C.
  2. temperatureThe mixture was refluxed for 15 hours
  3. customThe cooled reaction mixture
  4. washwas washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationthe dried solution concentrated at reduced pressure
  7. distillationThe residual oil was distilled

Sources & evidence

ORD record
ord-7c5e8ee883c24866ada84366a0f087f3
Source dataset
uspto-grants-1977_05
Patent number
US04021552

Reaction notes

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