Sodium Carbonate → HCID 18957840, compound

HRID 2379038Notes

Reaction equation

HRID 2379038 reaction equation
[Cl:1][C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1.CN(C)C(=O)C.Cl.Cl[CH2:19][C:20]1[N:21]=[C:22]([CH3:25])[S:23][CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+]>O>[Cl:1][C:2]1[N:6]([CH2:19][C:20]2[N:21]=[C:22]([CH3:25])[S:23][CH:24]=2)[C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 31374DimethylacetamideHCID 785722-ChlorobenzimidazoleHCID 27342034-(Chloromethyl)-2-methyl-1,3-thiazole--hydrogen chloride (1/1)

Product 1

HCID 18957840HCID 18957840, compoundYield 42.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

To a mixture of 15.5 pans of 2-chloro-1H-benzimidazole and 235 parts of N,N-dimethylacetamide there were added 22 pans of 4-(chloromethyl)-2-methylthiazole monohydrochloride and 25.4 pans of sodium carbonate. The whole was stirred for 18 hours at 75° C. and was then poured into water. The product was extracted with 4-methyl-2-pentanone and the extract was washed with water, dried, filtered and evaporated. The residue was crystallized from 2,2'-oxybispropane, yielding 11.3 parts (42.8%) of 2-chloro-1-[(2-methyl-4-thiazolyl)methyl]-1H-benzimidazole (interm. 1). In a similar manner there was also prepared 2-chloro-1-[(6-methyl-2-pyridinyl)methyl]1H-benzimidazole (interm. 2).

Workup

  1. extractionThe product was extracted with 4-methyl-2-pentanone
  2. washthe extract was washed with water
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was crystallized from 2,2'-oxybispropane

Sources & evidence

ORD record
ord-816830b7f6b54281add86b24329bb918
Source dataset
uspto-grants-1994_11
Patent number
US05360807

Reaction notes

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