Methylamine → HCID 19373114, compound

HRID 129004Notes

Reaction equation

HRID 129004 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[N:14]([C:15]=2[CH2:16][C:17]([OH:19])=O)[C:13]2[CH:20]=[C:21]([CH3:24])[CH:22]=[CH:23][C:12]=2[N:11]3[CH3:25])=[CH:4][CH:3]=1.[CH3:26][NH2:27]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]3[N:14]([C:15]=2[CH2:16][C:17]([NH:27][CH3:26])=[O:19])[C:13]2[CH:20]=[C:21]([CH3:24])[CH:22]=[CH:23][C:12]=2[N:11]3[CH3:25])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 19373113HCID 19373113, compound

Product 1

HCID 19373114HCID 19373114, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under a nitrogen stream, a suspension of 1.0 g (0.0028 mol) of 2-(4-chlorophenyl)-6,9-dimethyl-9H-imidazo[1,2-a]benzimidazole-3-acetic acid is prepared in 50 ml of dry tetrahydrofuran. 1.0 g (0.0063 mol) of N,N'-carbonyldiimidazole in solution in 50 ml of dry tetrahydrofuran is added and the mixture is stirred for 6 h. The solution is then treated with an excess of dry gaseous methylamine and again stirred for 4 h. The solvent is evaporated under reduced pressure. The residue is taken up in water, drained, washed with water and dried. 0.65 g of product is obtained which is purified by silica gel column chromatography, eluting with a chloroform/acetone 93/7 mixture. 0.26 g of compound is finally isolated. Melting point: 258°-260° C.

Workup

  1. stirringagain stirred for 4 h
  2. customThe solvent is evaporated under reduced pressure
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-bc66b5d3dc344565a6d2886193bc5090
Source dataset
uspto-grants-1995_11
Patent number
US05466706

Reaction notes

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