Dichloromethane → HCID 14518411, compound

HRID 1723095Notes

Reaction equation

HRID 1723095 reaction equation
[CH2:1]([N:4]1[C:8]2[CH:9]=[CH:10][C:11]([CH2:13]O)=[CH:12][C:7]=2[N:6]=[C:5]1[C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)[CH2:2][CH3:3].[Cl:21]CCl.CS(Cl)(=O)=O>C(N(CC)CC)C>[Cl:21][CH2:13][C:11]1[CH:10]=[CH:9][C:8]2[N:4]([CH2:1][CH2:2][CH3:3])[C:5]([C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)=[N:6][C:7]=2[CH:12]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 31297Methanesulfonyl chlorideHCID 14518387HCID 14518387, compound

Product 1

HCID 14518411HCID 14518411, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

(b-1) To a stirred solution of 4.01 parts of 1-propyl-2-(3-pyridinyl)-1H-benzimidazole-5-methanol in 65 parts of dichloromethane and 3 parts of N,N-diethylethanamine were added 2.23 parts of methanesulfonyl chloride. The whole was stirred for 45 minutes at room temperature. The mixture was poured into crushed ice and the dichloromethane layer was separated, dried, filtered and evaporated. The residue was dissolved in methylbenzene. The precipitate was filtered off and the filtrate was evaporated, yielding 2.3 parts (66%) of 5-(chloromethyl)-1-propyl-2-(3-pyridinyl)-1H-benzimidazole as a residue (int. 16).

Workup

  1. additionThe mixture was poured
  2. custominto crushed ice
  3. customthe dichloromethane layer was separated
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. dissolutionThe residue was dissolved in methylbenzene
  8. filtrationThe precipitate was filtered off
  9. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-fbff1ca70d7d4b88bd03d665bdd16017
Source dataset
uspto-grants-1989_08
Patent number
US04859684

Reaction notes

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