Ethylenethiourea → 5-[2-[(4,5-dihydro-1H-imidazol-2-yl)thio]ethyl]-1,4-dimethylpyrimido[1,6-a]indole

HRID 647596Notes

Reaction equation

HRID 647596 reaction equation
[NH:1]1[CH2:5][CH2:4][NH:3][C:2]1=[S:6].Br[CH2:8][CH2:9][C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]2[C:19]([CH3:24])=[N:20][CH:21]=[C:22]([CH3:23])[C:11]=12>O1CCOCC1>[NH:1]1[CH2:5][CH2:4][N:3]=[C:2]1[S:6][CH2:8][CH2:9][C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]2[C:19]([CH3:24])=[N:20][CH:21]=[C:22]([CH3:23])[C:11]=12

Participants

4

Reactant 2

HCID 2723650EthylenethioureaHCID 127081875-(2-Bromoethyl)-1,4-dimethylpyrimido[1,6-a]indole

Product 1

HCID 127864255-[2-[(4,5-dihydro-1H-imidazol-2-yl)thio]ethyl]-1,4-dimethylpyrimido[1,6-a]indoleYield 59.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-imidazolidinethione (3.1 g), 5-(2-bromoethyl)-1,4-dimethylpyrimido[1,6-a]indole (6 g, described in Example 13) and dry dioxane (400 ml) is refluxed for 6 hours. The resulting precipitate is collected by filtration and dissolved in water and the solution is neutralized with aqueous sodium bicarbonate. After adding a few drops of 10% sodium hydroxide, the aqueous mixture is extracted with chloroform. The combined extracts are washed with water, dried over magnesium sulfate, filtered and evaporated. The residue is crystallized from acetonitrile to obtain the title compound (3.8 g): mp 157°-159° C.; ir (CHCl3) 3400, 1610, 1595 and 1570 cm-1 ; uv(MeOH) λmax 250,299,311 and 325 nm; ε=35200, 4840, 8200, and 10870, respectively; and nmr (CDCl3) δ2.52(s), 2.99(s), 3.43(m), 3.60(s), 4.25(s) and 7.1-8.2(m).

Workup

  1. temperatureis refluxed for 6 hours
  2. filtrationThe resulting precipitate is collected by filtration
  3. dissolutiondissolved in water
  4. additionAfter adding a few drops of 10% sodium hydroxide
  5. extractionthe aqueous mixture is extracted with chloroform
  6. washThe combined extracts are washed with water
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue is crystallized from acetonitrile

Sources & evidence

ORD record
ord-69faabba0a1348ad9c150294311126af
Source dataset
uspto-grants-1983_10
Patent number
US04409224

Reaction notes

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