Tin tetrachloride → HCID 178480624, compound

HRID 2057078Notes

Reaction equation

HRID 2057078 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]=1[CH2:10][C:11]([O:13]CC)=O.[NH2:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]2[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]2)=[CH:19][C:18]=1[C:30]#[N:31].Cl[Sn](Cl)(Cl)Cl>ClCCCl>[CH3:29][N:26]1[CH2:25][CH2:24][N:23]([C:20]2[CH:21]=[CH:22][C:17]3[C:18](=[C:30]([NH2:31])[C:10]([C:11]([N:16]=3)=[O:13])=[C:2]3[NH:1][C:5]4[C:4](=[CH:9][CH:8]=[CH:7][CH:6]=4)[NH:3]3)[CH:19]=2)[CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 24287Tin tetrachlorideHCID 308071ethyl 2-(1H-1,3-benzodiazol-2-yl)acetateHCID 219285192-Amino-5-(4-methyl-1-piperazinyl)benzonitrile

Product 1

HCID 178480624HCID 178480624, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

Ethyl 2-benzimidazol-2-ylacetate (1.1 eq) and 2-amino-5-(4-methylpiperazinyl)benzenecarbonitrile (1.0 eq) were dissolved in 1,2-dichloroethane, and then SnCl4 (11 eq) was added. The mixture was heated at reflux overnight. Upon cooling, the mixture was concentrated in vacuo. NaOH (3 M) was added to the solid, and the mixture heated at 80° C. for 0.5 hours. The solid was filtered and washed sequentially with H2O, CH2Cl2, and acetone. LC/MS indicated that the product was present in the acetone layer and the solid. These fractions were combined and purified by silica gel chromatography (5-10% MeOH in CH2Cl2 with 1% Et3N) to give the desired product. LC/MS m/z 375.4 (MH+), Rt 1.65 minutes.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. temperatureUpon cooling
  4. concentrationthe mixture was concentrated in vacuo
  5. additionNaOH (3 M) was added to the solid
  6. filtrationThe solid was filtered
  7. washwashed sequentially with H2O, CH2Cl2, and acetone
  8. custompurified by silica gel chromatography (5-10% MeOH in CH2Cl2 with 1% Et3N)

Sources & evidence

ORD record
ord-da8b64aff244439aa54421549d281834
Source dataset
uspto-grants-2008_02
Patent number
US07335774B2

Reaction notes

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