Water → HCID 13345142, compound

HRID 1462021Notes

Reaction equation

HRID 1462021 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[CH2:12][CH2:11][N:10]([CH:13]([CH3:16])[CH2:14]O)[CH2:9][CH2:8]1.P(Br)(Br)[Br:18].O>C(Cl)(Cl)Cl>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[CH2:12][CH2:11][N:10]([CH:13]([CH3:16])[CH2:14][Br:18])[CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 962WaterHCID 24614Phosphorus tribromideHCID 13345141HCID 13345141, compound

Product 1

HCID 13345142HCID 13345142, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

The alcohol prepared in Part (b) hereinabove, (30 grams; 0.136 moles), diluted with 40 ml of chloroform is added dropwise to 15 cc of phosphorus tribromide. The mixture is warmed to about 60° C. for 2 hours. The mixture is then cooled to below 0° C. and the excess of the reagent is decomposed with water. The mixture is made alkaline, the organic phase is separated and the aqueous phase extracted with chloroform. The total organic phase is combined, dried and allowed to evaporate, giving as a residue a yellow solid material, which after recrystallization gives Compound (c) with m.p. 50°-51° C. from n-hexane; Rf=0.54 (from ethyl acetate); IR (nujol) νmax: 1600, 1490, 1445, 1320, 1260, 785 cm-1 ; Br (Schoeninger)--Calculated %: 28.1--Found %: 27.9.

Workup

  1. temperatureThe mixture is then cooled to below 0° C.
  2. customthe organic phase is separated
  3. extractionthe aqueous phase extracted with chloroform
  4. customdried
  5. customto evaporate
  6. customgiving as a residue a yellow solid material, which
  7. customafter recrystallization

Sources & evidence

ORD record
ord-faf3d7347ff647ff95e53299af7d5e31
Source dataset
uspto-grants-1984_07
Patent number
US04457931

Reaction notes

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