HCID 18799436, compound → HCID 18799398, compound

HRID 1637625Notes

Reaction equation

HRID 1637625 reaction equation
[Cl:1][C:2]1[C:3]([CH2:14]Cl)=[N:4][CH:5]=[CH:6][C:7]=1[N:8]([CH3:13])[CH2:9][CH2:10][CH2:11][OH:12].[SH:16][C:17]1[NH:18][C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=2[N:21]=1>CC(O)C>[NH:18]1[C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=2[N:21]=[C:17]1[S:16][CH2:14][C:3]1[C:2]([Cl:1])=[C:7]([N:8]([CH3:13])[CH2:9][CH2:10][CH2:11][OH:12])[CH:6]=[CH:5][N:4]=1

Participants

4

Reactant 2

HCID 18799436HCID 18799436, compoundHCID 178527775HCID 178527775, compound

Product 1

HCID 18799398HCID 18799398, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
4 °C

Procedure

A solution of 3-[(3-chloro-2-chloromethyl-pyridin-4-yl)-methyl-amino]-propanol isolated in step a) (5.3 g) and 2-mercapto-benzimidazole (2.2 g, 14.6 mmol) in 2-propanol (150 ml) is boiled under reflux for 2 h. After cooling to 4° C. the precipitate is filtered, washed with 2-propanol and dried in vacua. The residue is dissolved in water, adjusted to pH 8 with aqueous sodium bicarbonate solution and extracted with ethyl acetate. The combined organic extracts are washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue is crystallized from ethyl acetate to give the title compound as an off-white solid, 3.6 g (46%). M.p. 127-30° C.

Workup

  1. temperatureunder reflux for 2 h
  2. filtrationis filtered
  3. washwashed with 2-propanol
  4. customdried in vacua
  5. dissolutionThe residue is dissolved in water
  6. extractionextracted with ethyl acetate
  7. washThe combined organic extracts are washed with water
  8. dry with materialdried over magnesium sulfate
  9. customevaporated in vacuo
  10. customThe residue is crystallized from ethyl acetate

Sources & evidence

ORD record
ord-ff764baf42524ec0936ee8264dabac13
Source dataset
uspto-grants-2000_03
Patent number
US06043242

Reaction notes

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