Benzyl Alcohol → HCID 15332171, compound

HRID 987890Notes

Reaction equation

HRID 987890 reaction equation
[H-].[Na+].Cl[C:4]1[N:5]=[N:6][C:7]([NH:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[CH:8][CH:9]=1.O.[CH2:17]([OH:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[CH2:17]([O:24][C:4]1[N:5]=[N:6][C:7]([NH:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[CH:8][CH:9]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 24758Sodium hydrideHCID 15332170N-(6-Chloropyridazin-3-yl)-beta-alanine

Product 1

HCID 15332171HCID 15332171, compoundYield 47%

Conditions

Temperature
180 °C

Procedure

Sodium hydride (22.0 mmol, 0.88 g) was dissolved in benzyl alcohol (10 mL). To the resulting solution was added N-(3-chloropyridazin-6-yl)-3-aminopropionic acid (10.0 mmol, 2.01 g), and the mixture was heated to about 165° C. (oil bath 180° C.) for 3 hours. After cooling to room temperature, water (120 mL) was added, and the aqueous phase was extracted with dichloromethane (3×50 mL). The pH was adjusted to 4.0 with 2M aqueous hydrochloric acid. The light brown precipitate was filtered, washed with water (2×1 mL) and dried over phosphorus pentoxide. The resulting solid was dried to give 1.36 g (47%) of the title compound. The product was pure according to TLC Rf 0.16 (dichloromethane/methanol/acetic acid, 85:10:5).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionthe aqueous phase was extracted with dichloromethane (3×50 mL)
  3. filtrationThe light brown precipitate was filtered
  4. washwashed with water (2×1 mL)
  5. dry with materialdried over phosphorus pentoxide
  6. customThe resulting solid was dried

Sources & evidence

ORD record
ord-c739f5cf282040cb853abe096b184d7a
Source dataset
uspto-grants-2003_10
Patent number
US06632919B1

Reaction notes

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