3-Iodoaniline → HCID 21955984, compound

HRID 2212874Notes

Reaction equation

HRID 2212874 reaction equation
CS([C:4]1[N:9]=[C:8]([C:10]2[S:14][C:13]([NH2:15])=[N:12][C:11]=2[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:7]=[CH:6][N:5]=1)=O.[I:22][C:23]1[CH:24]=[C:25]([CH:27]=[CH:28][CH:29]=1)[NH2:26]>B(F)(F)F.CCOCC>[NH2:15][C:13]1[S:14][C:10]([C:8]2[CH:7]=[CH:6][N:5]=[C:4]([NH:26][C:25]3[CH:27]=[CH:28][CH:29]=[C:23]([I:22])[CH:24]=3)[N:9]=2)=[C:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:12]=1

Participants

4

Reactant 2

HCID 122713-IodoanilineHCID 21955954HCID 21955954, compound

Product 1

HCID 21955984HCID 21955984, compound

Reagents, catalysts & solvents 1

HCID 8000Boron trifluoride etherateCatalyst

Procedure

A mixture of 5-(2-methylsulfinyl-pyrimidin-4-yl)-4-phenyl-2-amino-thiazole (2.0 g, 6.3 mmol) and m-iodoaniline (7.0 g, 31.6 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 N-[4-(2-amino-4-phenyl-thiazol-5-yl)-pyrimidin-2-yl]-N-(3-iodo-phenyl)-amine after chromatography (eluent: 2:1 mixture of ethyl acetate/hexane) has a m.p. of 243–244° 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. additionThe N-[4-(2-amino-4-phenyl-thiazol-5-yl)-pyrimidin-2-yl]-N-(3-iodo-phenyl)-amine after chromatography (eluent: 2:1 mixture of ethyl acetate/hexane)

Sources & evidence

ORD record
ord-80b7646a8f6d4ed499ed2d2517d08f81
Source dataset
uspto-grants-2006_09
Patent number
US07105517B2

Reaction notes

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