Butylamine → 85262-77-7

HRID 637846Notes

Reaction equation

HRID 637846 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Cl:12])[CH:11]=1)[O:5][CH2:6][CH2:7]Br.[CH2:13]([NH2:17])[CH2:14][CH2:15][CH3:16]>>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Cl:12])[CH:11]=1)[O:5][CH2:6][CH2:7][NH:17][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

3

Reactant 2

HCID 8007ButylamineHCID 222467761-(2-Bromoethoxy)-3,5-dichlorobenzene

Product 1

HCID 2025633585262-77-7Yield 51.5%

Procedure

A solution of 33.76 g (0.126 mole) of 2-(3,5-dichlorophenoxy)-1-bromoethane in 200 ml of n-butylamine was stirred at 25° C. for 20 hr. The excess n-butylamine was evaporated in vacuo, and the residue was suspended in a mixture of dilute sodium hydroxide and shaken with methylene chloride. The methylene chloride layer was extracted in sequence with two additional portions of dilute sodium hydroxide, one of dilute sulfuric acid and once more with dilute sodium hydroxide. The volume of the methylene chloride layer was reduced to about 150 ml and excess ethereal hydrogen chloride was added. Addition of anhydrous ether gave a white precipitate which was collected and dried under high vacuum (78° C.) to give 19.35 g (51.5%) white crystals, m.p. 195°-196° C.

Workup

  1. customThe excess n-butylamine was evaporated in vacuo
  2. additionthe residue was suspended in a mixture of dilute sodium hydroxide
  3. extractionThe methylene chloride layer was extracted in sequence with two additional portions of dilute sodium hydroxide, one of dilute sulfuric acid and once more with dilute sodium hydroxide
  4. additionwas added
  5. additionAddition of anhydrous ether
  6. customgave a white precipitate which
  7. customwas collected
  8. customdried under high vacuum (78° C.)

Sources & evidence

ORD record
ord-ae30cefc6ff14b7a957476324a2ea9c8
Source dataset
uspto-grants-1985_12
Patent number
US04558155

Reaction notes

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