4-Hydroxybenzoic Acid → 937842-55-2

HRID 1009834Notes

Reaction equation

HRID 1009834 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.[NH:11]1[CH2:14][CH2:13][CH2:12]1>C(#N)C>[N:11]1([C:6]([C:5]2[CH:4]=[CH:3][C:2]([OH:1])=[CH:10][CH:9]=2)=[O:8])[CH2:14][CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 1354-Hydroxybenzoic AcidHCID 10422Azetidine2×

Product 1

HCID 24764369937842-55-2Yield 65%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
50 °C

Procedure

1,1-Carbonyldiimidazole (95.57 mmol; 16.57 g) was charged to a 250 mL round bottomed flask purged with nitrogen, acetonitrile (72 mL) was added, to form a mobile white slurry. 4-Hydroxybenzoic acid (86.88 mol; 12.00 g) was added in portions over 30 minutes to give clear yellow solution, which then became a slurry after approximately 15 minutes. The slurry was heated to 50° C. and azetidine (104.25 mol; 5.95 g) in acetonitrile (10 mL) was added drop wise over 10 minutes. Further azetidine (17.38 mmol; 992.08 mg) was added in acetonitrile (12 mL) and the reaction mixture was heated to 50° C. for a further hour. The precipitated product (10 g, 65% yield) was isolated by filtration and washed with acetonitrile (15 mL) and then dried in a vacuum oven at 40° C.

Workup

  1. custompurged with nitrogen, acetonitrile (72 mL)
  2. additionwas added
  3. customto form a mobile white slurry
  4. customto give clear yellow solution, which
  5. customafter approximately 15 minutes
  6. temperaturethe reaction mixture was heated to 50° C. for a further hour

Sources & evidence

ORD record
ord-e9e16c8b80214d6fb510b4350231e959
Source dataset
uspto-grants-2011_07
Patent number
US07973178B2

Reaction notes

Loading…