Cyanogen Bromide → HCID 13656116, compound

HRID 746046Notes

Reaction equation

HRID 746046 reaction equation
[N:1]#[C:2]Br.[C:4]1([C:10]2([CH2:19][CH2:20][N:21](C)[CH3:22])[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[O:12][CH2:11]2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(Cl)(Cl)Cl>[C:4]1([C:10]2([CH2:19][CH2:20][N:21]([C:2]#[N:1])[CH3:22])[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[O:12][CH2:11]2)[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 13656115HCID 13656115, compound

Product 1

HCID 13656116HCID 13656116, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 10.9 g (103 mmole) cyanogen bromide and 23 g (86 mmole) of 2-(3-phenyl-2,3-dihydrobenzofuran-3-yl)-N,N-dimethylethylamine in 500 ml CHCl3 was refluxed for 4 hours. The solvent was evaporated and the resultant oil warmed to reflux in 500 ml water. After cooling, the mixture was extracted with CH2Cl2 (2×1 liter), and the organics were washed with 1N HOAc (3×1 liter) and dried over K2CO3. Evaporation gave 20 g of an oil, which was chromatographed on 200 g silica gel using CH2Cl2 as an eluent to give 11 g of an oil which solidified on standing. Recrystallization from acetone/hexane gave 7.1 g (30%) of crystals, m.p. 88°-92°.

Workup

  1. customThe solvent was evaporated
  2. temperaturethe resultant oil warmed
  3. temperatureto reflux in 500 ml water
  4. temperatureAfter cooling
  5. extractionthe mixture was extracted with CH2Cl2 (2×1 liter)
  6. washthe organics were washed with 1N HOAc (3×1 liter)
  7. dry with materialdried over K2CO3
  8. customEvaporation

Sources & evidence

ORD record
ord-e92204d05e2e48dd93784b5b84b9ad1b
Source dataset
uspto-grants-1986_07
Patent number
US04602035

Reaction notes

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