Formaldehyde → HCID 18628520, compound

HRID 1060529Notes

Reaction equation

HRID 1060529 reaction equation
[NH2:1][N:2]([CH2:16][CH2:17][OH:18])[C:3]([NH:5][C:6]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([Cl:14])=[CH:8][C:7]=1[Cl:15])=[O:4].[CH2:19]=O>C(Cl)Cl>[Cl:15][C:7]1[CH:8]=[C:9]([Cl:14])[C:10]([O:12][CH3:13])=[CH:11][C:6]=1[NH:5][C:3]([N:2]1[CH2:16][CH2:17][O:18][CH2:19][NH:1]1)=[O:4]

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 70032399HCID 70032399, compound

Product 1

HCID 18628520HCID 18628520, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
42 °C

Procedure

A mixture of 29.4 g (0.1 mol) of N-amino-N-2-hydroxyethyl-N′-(2,4-dichloro-5-methoxyphenyl)urea and 9 g (0.11 mol) of a 37% strength formaldehyde solution in 500 ml of methylene chloride was stirred at 42° C. for 2 h. After cooling, the reaction mixture was filtered with suction with about 300 ml of silica gel and washed with methylene chloride. Analysis by thin-layer chromatography gave a higher Rf value than that of the reaction mixture which had not been treated with silica gel and remained on the methyleneimino stage. Concentration under reduced pressure gave 27.8 g (81.8% of theory) of the title compound of m.p. 128-130° C.

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction mixture was filtered with suction with about 300 ml of silica gel
  3. washwashed with methylene chloride
  4. customAnalysis by thin-layer chromatography gave a higher Rf value than that of the reaction mixture which
  5. additionhad not been treated with silica gel
  6. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-348e5cc46da64392834f9a93f777e9ad
Source dataset
uspto-grants-2003_02
Patent number
US06525000B1

Reaction notes

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