4-Chlorobenzene-1-carboximidamide hydrochloride → 2-(4-Chlorophenyl)-4,5-bis(4-methoxyphenyl)pyrimidine

HRID 615583Notes

Reaction equation

HRID 615583 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:11]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)=[CH:12]N(C)C)=O)=[CH:5][CH:4]=1.Cl.[Cl:25][C:26]1[CH:34]=[CH:33][C:29]([C:30]([NH2:32])=[NH:31])=[CH:28][CH:27]=1.CC(C)([O-])C.[K+]>C1(C)C=CC=CC=1>[Cl:25][C:26]1[CH:34]=[CH:33][C:29]([C:30]2[N:32]=[C:9]([C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=3)[C:11]([C:16]3[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=3)=[CH:12][N:31]=2)=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 2034364-Chlorobenzene-1-carboximidamide hydrochlorideHCID 4590694HCID 4590694, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 133930512-(4-Chlorophenyl)-4,5-bis(4-methoxyphenyl)pyrimidine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 9.34 g. of (4-methoxyphenyl)-[1-(4-methoxyphenyl)-2-dimethylaminovinyl]ketone, 5.73 g. of 4-chlorobenzamidine hydrochloride, and 6.73 g. of potassium t-butoxide in 200 ml. of toluene was allowed to reflux for 2.5 hours and then stirred overnight at room temperature. The suspension was extracted twice each with 200 ml. of water. The combined water extracts were back-extracted with 100 ml. of toluene. The combined toluene solutions were washed with 100 ml. of a saturated sodium chloride solution. The organic solution was then dried over sodium sulfate and evaporated in vacuo. The residue was purified by chromatography over silica gel. The appropriate fractions were evaporated to dryness and crystallized from Skelly B to provide 3.97 g. of the desired title product, m.p. about 151°-153° C.

Workup

  1. additionA suspension of 9.34 g
  2. temperatureto reflux for 2.5 hours
  3. extractionThe suspension was extracted twice each with 200 ml
  4. extractionThe combined water extracts were back-extracted with 100 ml
  5. washThe combined toluene solutions were washed with 100 ml
  6. dry with materialThe organic solution was then dried over sodium sulfate
  7. customevaporated in vacuo
  8. customThe residue was purified by chromatography over silica gel
  9. customThe appropriate fractions were evaporated to dryness
  10. customcrystallized from Skelly B
  11. customto provide 3.97 g

Sources & evidence

ORD record
ord-26cdc7ee29424e529d74bd6f17c50fc6
Source dataset
uspto-grants-1985_02
Patent number
US04500533

Reaction notes

Loading…