Chloral → HCID 12906108, compound

HRID 596729Notes

Reaction equation

HRID 596729 reaction equation
[O:1]([C:8]1[CH:14]=[CH:13][C:11]([NH2:12])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:15][N:16]=[C:17]=[O:18].O=[CH:20][C:21]([Cl:24])([Cl:23])[Cl:22].S(Cl)([Cl:27])=O>C(Cl)Cl.COCCOC>[CH3:15][N:16]([CH:20]([Cl:27])[C:21]([Cl:24])([Cl:23])[Cl:22])[C:17]([NH:12][C:11]1[CH:10]=[CH:9][C:8]([O:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:14][CH:13]=1)=[O:18]

Participants

7

Reactant 4

HCID 6407ChloralHCID 8764(4-Aminophenoxy)benzeneHCID 12228Methyl IsocyanateHCID 24386Thionyl Chloride

Product 1

HCID 12906108HCID 12906108, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

p-Phenoxyaniline (11.7 g, 0.063 mol) was dissolved in 25 ml. 1,2-dimethoxyethane (Ansul E-121) and heated to 65° C. Methyl isocyanate (3.7 g, 0.65 mol) was added over a period of 10 minutes. Heating and stirring were continued for 1 hour. Then chloral (14.8 g, 0.1 mol) was added to the hot solution, followed immediately by the addition of 11.9 g (0.1 mol) thionyl chloride. It was kept at 65° C. for 41/2 hours. The solution was cooled to 40°, and 25 ml of methylene chloride was added. The solution was refluxed for one more hour and then allowed to cool. The solid which formed upon cooling was filtered, washed with methylene chloride to give 5.0 g (20% yield) of the product, as a white powder, melting point 165°-167° C. A second crop, melting point 160°-162° C., weighed 5.5 g (22%). Elemental analysis showed: %Cl, calc. 34.8, found 34.4; %N, calc. 6.9, found 6.8; %C, calc. 47.1, found 47.5; %H, calc. 3.46, found 3.3. The product is the eighth compound tabulated in Table I.

Workup

  1. temperatureHeating
  2. customwas kept at 65° C. for 41
  3. custom2 hours
  4. temperatureThe solution was cooled to 40°
  5. temperatureThe solution was refluxed for one more hour
  6. temperatureto cool
  7. customThe solid which formed
  8. temperatureupon cooling
  9. filtrationwas filtered
  10. washwashed with methylene chloride

Sources & evidence

ORD record
ord-b96ccadb920840f38131dba045c93215
Source dataset
uspto-grants-1977_03
Patent number
US04012225

Reaction notes

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