1-Pentene, 5-bromo- → HCID 178446235, compound

HRID 486623Notes

Reaction equation

HRID 486623 reaction equation
[CH2:1]([C:5]1[NH:6][C:7]2[C:12]([C:13](=[O:15])[N:14]=1)=[CH:11][C:10]([C:16]1[NH:20][N:19]=[N:18][N:17]=1)=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH3:4].Br[CH2:22][CH2:23][CH2:24][CH:25]=[CH2:26].C(N(CC)C(C)C)(C)C>O1CCCC1>[CH2:1]([C:5]1[NH:6][C:7]2[C:12]([C:13](=[O:15])[N:14]=1)=[CH:11][C:10]([C:16]1[N:17]=[N:18][N:19]([CH2:26][CH2:25][CH2:24][CH:23]=[CH2:22])[N:20]=1)=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 707041-Pentene, 5-bromo-HCID 81531DiisopropylethylamineHCID 178441834HCID 178441834, compound

Product 1

HCID 178446235HCID 178446235, compoundYield 53.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3.0 g of 2-butyl-6-(1H-tetrazol-5-yl)-4(1H)-quinazolinone, 2.2 g of 5-bromo-1-pentene and 2 ml of N,N-diisopropylethylamine in 50 ml of tetrahydrofuran is refluxed for 24 hours. The volatiles are evaporated in vacuo to a residue which is partitioned between chloroform and water. The organic layer is dried over MgSO4, filtered and evaporated in vacuo to a residue which is purified by column chromatography on silica gel by elution with 3:2 ethyl acetate-hexanes to give a residue which crystallizes from ethyl acetate-hexanes to give 2.0 g of the desired product as a solid, m.p. 130° C.

Workup

  1. temperatureis refluxed for 24 hours
  2. customThe volatiles are evaporated in vacuo to a residue which
  3. customis partitioned between chloroform and water
  4. dry with materialThe organic layer is dried over MgSO4
  5. filtrationfiltered
  6. customevaporated in vacuo to a residue which
  7. customis purified by column chromatography on silica gel by elution with 3:2 ethyl acetate-hexanes
  8. customto give a residue which
  9. customcrystallizes from ethyl acetate-hexanes

Sources & evidence

ORD record
ord-2c45c55aabea42ffadadf03a5979cda0
Source dataset
uspto-grants-1994_03
Patent number
US05292742

Reaction notes

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