Chloral → HCID 12906108, compound

HRID 1763205Notes

Reaction equation

HRID 1763205 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>COCCOC.C(Cl)Cl>[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

Conditions

Temperature
65 °C

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 4 1/2 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 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 34.35; %N, calc. 6.9, found 6.8; %C, calc., 47.1, found 47.5; %H, calc. 3.46, found 3.3.

Workup

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

Sources & evidence

ORD record
ord-7c44f815f1d0431da7c89200647866d8
Source dataset
uspto-grants-1978_09
Patent number
US04111683

Reaction notes

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