Benzimidazole → HCID 59846324, compound

HRID 1363235Notes

Reaction equation

HRID 1363235 reaction equation
Cl[C:2]1[N:7]=[C:6]([S:8][C:9]#[N:10])[C:5]([N+:11]([O-:13])=[O:12])=[CH:4][N:3]=1.[N:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[NH:16][CH:15]=1.CCN(CC)CC>CN(C=O)C>[N+:11]([C:5]1[C:6]([S:8][C:9]#[N:10])=[N:7][C:2]([N:14]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[N:16]=[CH:15]2)=[N:3][CH:4]=1)([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 5798BenzimidazoleHCID 8471TriethylamineHCID 210775882-Chloro-5-nitropyrimidin-4-yl thiocyanate

Product 1

HCID 59846324HCID 59846324, compoundYield 45.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-chloro-5-nitro-4-thiocyanatopyrimidine (5.0 g, 23 mmol, WO 2003/032994) and benzimidazole (2.72 g, 23 mmol) in 200 mL of DMF was cooled to 0 C and Et3N (2.33 g, 23 mmol) was added. The ice-bath was removed and the contents were stirred for 3 h at RT. The reaction mixture was diluted with water and filtered. The solid was washed with water, followed by ice-cold methanol and dried in vacuo to provide 3.1 g of 1-(5-nitro-4-thiocyanatopyrimidin-2-yl)benzimidazole. 1H NMR (300 MHz, DMSO-d6) □□ 9.70 (s, 1H), 9.15 (s, 1H), 8.90-8.80 (m, 1H), 7.95-7.80 (m, 1H), 7.55-7.35 (m, 2H).

Workup

  1. additionwas added
  2. customThe ice-bath was removed
  3. additionThe reaction mixture was diluted with water
  4. filtrationfiltered
  5. washThe solid was washed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-67ba9240c4f242ab817060db3d2ddc85
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

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