Potassium Iodide → HCID 15037345, compound

HRID 704720Notes

Reaction equation

HRID 704720 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][CH:11]1[CH2:15][CH2:14][N:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:12]1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+].Cl.Cl[CH2:31][C:32]1[N:33]=[CH:34][S:35][CH:36]=1>O.CN(C)C(=O)C>[S:35]1[CH:36]=[C:32]([CH2:31][N:1]2[C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N:3]=[C:2]2[NH:10][CH:11]2[CH2:15][CH2:14][N:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:12]2)[N:33]=[CH:34]1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 27632894-(Chloromethyl)-1,3-thiazole hydrochlorideHCID 15037349HCID 15037349, compound

Product 1

HCID 15037345HCID 15037345, compoundYield 69.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

To a stirred mixture of 5.5 parts of ethyl 3-(1H-benzimidazol-2-ylamino)-1-pyrrolidinecarboxylate, 6.4 parts of sodium carbonate, 0.1 parts of potassium iodide and 81 parts of N,N-dimethylacetamide were added portionwise 4.3 parts of 4-(chloromethyl)thiazole hydrochloride at 130° C. Upon completion, stirring was continued for 3 hours at 130° C. After cooling, the reaction mixture was poured into 450 parts of water. The product was extracted twice with methylbenzene. The combined extracts were washed with water, dried, filtered and evaporated, yielding 5.2 parts (69.9%) of ethyl 3-[[1-(4-thiazolylmethyl)-1H-benzimidazol-2-yl]amino]-1-pyrrolidinecarboxylate as an oily residue (compound 32).

Workup

  1. temperatureAfter cooling
  2. extractionThe product was extracted twice with methylbenzene
  3. washThe combined extracts were washed with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-d4424a449bc944b39eb9bdef4a233a09
Source dataset
uspto-grants-1991_01
Patent number
US04988689

Reaction notes

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