Potassium Carbonate → HCID 12786469, compound

HRID 1660345Notes

Reaction equation

HRID 1660345 reaction equation
[Cl:1][CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]2[C:13]([CH3:18])=[N:14][CH:15]=[C:16]([CH3:17])[C:5]=12.Br[N:20]1[C:24](=[O:25])[CH2:23][CH2:22][C:21]1=[O:26].C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl>[Cl:1][CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]2[C:13]([CH3:18])=[N:14][C:15]([N:20]3[C:24](=[O:25])[CH2:23][CH2:22][C:21]3=[O:26])=[C:16]([CH3:17])[C:5]=12

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 67184N-bromobutanimideHCID 12708186HCID 12708186, compound

Product 1

HCID 12786469HCID 12786469, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a refluxing solution of 5-(2-chloroethyl)-1,4-dimethylpyrimido[1,6-a]indole (13 g, described in Example 12), in chloroform (400 ml) is added N-bromosuccinimide (9.4 g) and anhydrous potassium carbonate (7 g). The reaction mixture is stirred and refluxed for 45 minutes. The resulting slurry is cooled and washed with water, and the organic phase is separated and evaporated. The residue is chromatographed on silica gel using chloroform and the eluates are evaporated. The residue (6.6 g) is crystallized from ethyl acetate to give 1-[5-(2-chloro)ethyl-1,4-dimethylpyrimido[1,6-a]indol-3-yl]pyrrolidine-2,5-dione; mp 232°-234° C.; ir (CHCl3) 1780 (weak) and 1705 cm-1 ; uv (MeOH) λmax 299, 310, and 324 nm; ε=6300, 10180, and 13170, respectively; nmr (CDCl3) δ2.31(s), 2.82(s), 2.91(s), 3.55(m), 7.0(m) and 8.0(m).

Workup

  1. temperaturerefluxed for 45 minutes
  2. temperatureThe resulting slurry is cooled
  3. washwashed with water
  4. customthe organic phase is separated
  5. customevaporated
  6. customThe residue is chromatographed on silica gel
  7. customthe eluates are evaporated
  8. customThe residue (6.6 g) is crystallized from ethyl acetate

Sources & evidence

ORD record
ord-7aad4a2992bb48a89ea4850094f80538
Source dataset
uspto-grants-1981_12
Patent number
US04307234

Reaction notes

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