Formaldehyde → HCID 13121256, compound

HRID 1701989Notes

Reaction equation

HRID 1701989 reaction equation
[C:1]1([NH:7][NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)O.[CH2:14]=O.[C:16]1([CH:22]=[CH2:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O.C(O)(=O)C>[C:1]1([N:7]2[CH:22]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:23][CH2:14][NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 1118Sulfuric AcidHCID 7501StyreneHCID 7516Phenylhydrazine

Product 1

HCID 13121256HCID 13121256, compoundYield 60.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

Phenylhydrazine (108.14 g, 1 mole) is added dropwise to a cooled (4°-8° C.) and stirred mixture of concentrated sulfuric acid (147 g, 1.5 moles), glacial acetic acid (200 ml) and water (25 ml). Paraformaldehyde (30.03 g, 1 mole) and phenylethylene (104.1 g, 1 mole) are added simultaneously during 1 hr at 25° C. and stirring is continued for 2 hr at 30° C. Water (500 ml) is added and the aqueous dark solution is washed with benzene. The aqueous layer is basified with 50% sodium hydroxide and extracted with benzene. The organic extracts are combined, dried over magnesium sulfate and evaporated. The residue is distilled at 170° C. 0.6 torr to give a distillate of the title compound (135.9 g). The title compound is dissolved in diethyl ether and dry hydrogen chloride is added. The precipitate is collected and crystallized from methanol-diethyl ether to obtain the hydrochloride salt of the title compound, mp 212°-214° C.

Workup

  1. temperaturea cooled (4°-8° C.)
  2. stirringstirring
  3. washthe aqueous dark solution is washed with benzene
  4. extractionextracted with benzene
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. distillationThe residue is distilled at 170° C

Sources & evidence

ORD record
ord-8448c3cab21042cfbccaea2f6275e7e8
Source dataset
uspto-grants-1983_04
Patent number
US04379926

Reaction notes

Loading…