Water → HCID 86747748, compound

HRID 128563Notes

Reaction equation

HRID 128563 reaction equation
[S:1](/[CH:4]=[CH:5]\[C:6]([OH:8])=[O:7])[C:2]#[N:3].C1CCN2C(=NCCC2)CC1.[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>C(#N)C>[S:1](/[CH:4]=[CH:5]\[C:6]([O:8][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:7])[C:2]#[N:3]

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 53838152-Propenoic acid, 3-thiocyanato-

Product 1

HCID 86747748HCID 86747748, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent3×

Procedure

To a stirred suspension of compound 2 (3.0 g., 0.023 mole) in dry acetonitrile (40 ml), a solution of DBU (3.54 g., 0.023 mole) in 10 ml of dry acetonitrile was added dropwise, keeping the temperature of the mixture below 25° C. To the resulting solution was added dropwise a solution of benzyl bromide (4.0 g., 0.023 mole) in 15 ml of dry acetonitrile at room temperature. After stirring for 5 hours, the mixture was poured into water, and extracted with ether. The ether extract was washed with water, dried (MgSO4) and concentrated to give an oil which solidified upon standing, 4.3 g. The solid recrystallized from ethanol/hexane mixture as plate-like crystals: mp 48.5°-50.5° C.; IR (KBr) 1695, 2180 cm-1.

Workup

  1. customthe temperature of the mixture below 25° C
  2. extractionextracted with ether
  3. extractionThe ether extract
  4. washwas washed with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customto give an oil which
  8. customThe solid recrystallized from ethanol/hexane mixture as plate-like crystals

Sources & evidence

ORD record
ord-5bc79786e05945ee90a2f902536062c8
Source dataset
uspto-grants-1995_11
Patent number
US05464832

Reaction notes

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