Sodium Hydroxide → HCID 178505473, compound

HRID 728640

Reaction equation

HRID 728640 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:5]2[NH:6][C:7]([SH:9])=[N:8][C:4]=2[CH:3]=1.Cl.[CH:13]1([CH2:16][O:17][C:18]2[CH:23]=[CH:22][N:21]=[C:20]([CH2:24]Cl)[CH:19]=2)[CH2:15][CH2:14]1.[OH-].[Na+]>O.CO>[F:1][C:2]1[CH:11]=[CH:10][C:5]2[NH:6][C:7]([S:9][CH2:24][C:20]3[CH:19]=[C:18]([O:17][CH2:16][CH:13]4[CH2:15][CH2:14]4)[CH:23]=[CH:22][N:21]=3)=[N:8][C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 193909394-Cyclopropylmethoxy-2-chloromethylpyridine hydrochlorideHCID 178505474HCID 178505474, compound

Product 1

HCID 178505473HCID 178505473, compoundYield 82.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent2×

Procedure

To 5-fluoro-2-mercapto-1H-benzimidazole (0.88 g, 0.0051 mol) in methanol (25 ml) NaOH (0.2 g, 0.0051 mol) dissolved in H2O (1 ml) and 4-cyclopropylmethoxy-2-chloromethylpyridine hydrochloride (0.91 g, 0.0046 mol) dissolved in methanol (10 ml) were added in the given order. The mixture was heated to boiling and NaOH (0.2 g, 0.005 mol) dissolved in H2O (1 ml) was added and the mixture was refluxed for 1 hour. After evaporation of methanol, CH2Cl2 (75 ml) and H2O (50 ml) were added and pH adjusted to 10. The mixture was vigorously stirred, the phases were separated, the organic phase was dried over Na2SO4 and evaporated giving the desired product (1.25 g, 72%). NMR data for the product is given below.

Workup

  1. additionwere added in the given order
  2. additionwas added
  3. temperaturethe mixture was refluxed for 1 hour
  4. customAfter evaporation of methanol, CH2Cl2 (75 ml) and H2O (50 ml)
  5. additionwere added
  6. customthe phases were separated
  7. dry with materialthe organic phase was dried over Na2SO4
  8. customevaporated

Sources & evidence

ORD record
ord-619cf0d7650044b68aaca58664d6dd1e
Source dataset
uspto-grants-1991_09
Patent number
US05049674

Linked notes

Loading…