Urea → HCID 178517487, compound

HRID 707219Notes

Reaction equation

HRID 707219 reaction equation
[NH2:1][C:2]([NH2:4])=[O:3].N[C:6]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:7]=1[CH:8]=O>O>[OH:3][C:2]1[N:4]=[CH:8][C:7]2[C:10](=[CH:11][C:12]([Cl:14])=[CH:13][CH:6]=2)[N:1]=1

Participants

4

Reactant 2

HCID 1176UreaHCID 112521382-Amino-4-chlorobenzaldehyde

Product 1

HCID 178517487HCID 178517487, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

Urea (115 g, 1915 mmol) was melted in a 500 mL 3 neck flask under nitrogen and heated at 160° C. The crude aminobenzaldehyde from step 1 (8.4 g) was added, one of the necks of the flask was opened to the atmosphere and the temperature of the oil bath raised to 190° C. When the bath temperature reached 175° C., a white precipitate was observed. The mixture was cooled and water (400 mL) was added. It was stirred for 15 minutes then filtered through a sintered glass frit. The collected solids were dried by azeotroping with toluene at reduced pressure (3×300 mL) then further dried under high vacuum at 70° C. The crude material was used without further purification.

Workup

  1. temperaturethe temperature of the oil bath raised to 190° C
  2. customreached 175° C.
  3. temperatureThe mixture was cooled
  4. filtrationthen filtered through a sintered glass frit
  5. customThe collected solids were dried
  6. customby azeotroping with toluene at reduced pressure (3×300 mL)
  7. customthen further dried under high vacuum at 70° C
  8. customThe crude material was used without further purification

Sources & evidence

ORD record
ord-a2b8963d2e1a4b349c5976f9c8f26f56
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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