Formaldehyde → HCID 21453998, compound

HRID 267542Notes

Reaction equation

HRID 267542 reaction equation
[CH2:1]=O.[NH2:3][CH2:4][CH:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[OH:6].C([O-])(=O)C.[Zn+2:17].[C:18]([O-])(=O)C.[C:22](=[S:24])=[S:23]>C(O)(C)C>[C:7]1([CH:5]2[O:6][CH2:1][N:3]([C:22]([S-:24])=[S:23])[CH2:4]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:7]1([CH:5]2[O:6][CH2:18][N:3]([C:22]([S-:24])=[S:23])[CH2:4]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[Zn+2:17]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 1000PhenylethanolamineHCID 6348Carbon DisulfideHCID 11192Zinc Acetate

Product 1

HCID 21453998HCID 21453998, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Conditions

Temperature
50 °C

Procedure

To 500 ml isopropanol was added 30 g. (1.0 mole) of paraformaldehyde and 137 g. (1.0 mole) of 2-amino-1-phenylethanol, and the resulting mixture was stirred and heated at 50°C. After the solids had all dissolved, the solution was stirred an additional 30 minutes at 50°C. To the solution, cooled to 35°C., was added 68.7 g. (0.375 mole) of anhydrous zinc acetate and 76.0 g. (1.0 mole) of carbon disulfide. Solids formed in several minutes whereby additional isopropanol (400 ml) was added to stir the mixture efficiently. After heating at 55°C. for two hours, the mixture was cooled and filtered; the resulting solids were washed several times in a Waring Blendor with water, and air-dried overnight to obtain 184 g (95%) of the desired product melting at 220°-223°C.; its IR spectrum was consistent with the structure.

Workup

  1. temperatureTo the solution, cooled to 35°C.
  2. additionwas added 68.7 g
  3. additionwas added
  4. stirringto stir the mixture efficiently
  5. temperatureAfter heating at 55°C. for two hours
  6. temperaturethe mixture was cooled
  7. filtrationfiltered
  8. washthe resulting solids were washed several times in a Waring Blendor with water
  9. customair-dried overnight

Sources & evidence

ORD record
ord-ff8a73e6ee44419aa480f0a0a6cec321
Source dataset
uspto-grants-1976_03
Patent number
US03943143

Reaction notes

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