Aniline → HCID 11267974, compound

HRID 2212871Notes

Reaction equation

HRID 2212871 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:13]2[CH:18]=[CH:17][N:16]=[C:15](S(C)=O)[N:14]=2)=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1.[NH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>B(F)(F)F.CCOCC>[NH2:1][C:2]1[S:3][C:4]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]([NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[N:14]=2)=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 21955954HCID 21955954, compound

Product 1

HCID 11267974HCID 11267974, compound

Reagents, catalysts & solvents 1

HCID 8000Boron trifluoride etherateCatalyst

Procedure

A mixture of 4-(2-amino-4-phenyl-thiazol-5-yl)-2-methylsulfinyl-pyrimidine (0.5 g, 1.58 mmol) and aniline (1.5 g, 15.8 mmol) is heated at +100° C. After the addition of boron trifluoride diethyl etherate (3 drops) the solution is heated at +150° C. for half an hour. On cooling the product starts to crystallize. The crystals are filtered and washed thoroughly with diethyl ether to give the N-[4-(2-amino-4-phenyl-thiazol-5-yl)-pyrimidin-2-yl]-N-phenyl-amine in pure form, having a m.p. of 244–245° C.

Workup

  1. temperatureis heated at +100° C
  2. temperatureis heated at +150° C. for half an hour
  3. temperatureOn cooling the product
  4. customto crystallize
  5. filtrationThe crystals are filtered
  6. washwashed thoroughly with diethyl ether

Sources & evidence

ORD record
ord-dc5c995d6f1d42b0bf21d079d82a14e5
Source dataset
uspto-grants-2006_09
Patent number
US07105517B2

Reaction notes

Loading…