1,3-Dichloro-2-isocyanatobenzene → HCID 12790784, compound

HRID 358341Notes

Reaction equation

HRID 358341 reaction equation
[NH2:1][CH:2]1[NH:7][CH2:6][CH:5]=[CH:4][NH:3]1.[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[C:10]=1[N:16]=[C:17]=[O:18]>CN(C=O)C.O>[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[C:10]=1[NH:16][C:17]([NH:1][C:2]1[NH:3][CH2:4][CH2:5][CH2:6][N:7]=1)=[O:18]

Participants

5

Reactant 2

HCID 6045371,3-Dichloro-2-isocyanatobenzeneHCID 5246742HCID 5246742, compound

Product 1

HCID 12790784HCID 12790784, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

A solution of 4.20 g (0.0424 mol) of 2-aminotetrahydropyrimidine in 30 ml of dry DMF was warmed to 70° C. and with stirring there was added 7.16 g (0.0381 mol) of 2,6-dichlorophenyl isocyanate in 25 ml of dry DMF over a period of 0.5 hours. After stirring for 2 hours at 70° C., the reaction mixture was cooled, diluted with H2O and filtered. The filter cake was washed well with H2O and air dried. The crude product, 5.1 g (47%) was dissolved in CH2Cl2, dried over K2CO3, filtered through a prewashed pad of filter aid and hexane was added to the cloud point. The resulting crystals were filtered, washed with hexane and dried in vacuo for 3 hours (50° C.; 5 mm Hg) to give pure N-(2,6-dichlorophenyl)-N'-(1,4,5,6-tetrahydropyrimidin-2-yl)urea, 4.71 g (43%); m.p. 179°-180.5° C. TLC: 5×20 cm silica gel; toluene-ether-MeOH (8:4:1) or CHCl3 --MeOH-NH4OH (90:10:1) indicated homogeneity; IR (KBr) 3421,1628 cm-1 ; UV max. (MeOH) 222 nm (ε=28300) and 239 nm (inflection) (ε=18,000).

Workup

  1. stirringAfter stirring for 2 hours at 70° C.
  2. temperaturethe reaction mixture was cooled
  3. filtrationfiltered
  4. washThe filter cake was washed well with H2O and air
  5. customdried
  6. dissolutionThe crude product, 5.1 g (47%) was dissolved in CH2Cl2
  7. dry with materialdried over K2CO3
  8. filtrationfiltered through a prewashed pad of filter aid and hexane
  9. additionwas added to the cloud point
  10. filtrationThe resulting crystals were filtered
  11. washwashed with hexane
  12. customdried in vacuo for 3 hours (50° C.; 5 mm Hg)

Sources & evidence

ORD record
ord-be7b09fbcb55423399439b2cb68a07bc
Source dataset
uspto-grants-1984_08
Patent number
US04466966

Reaction notes

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