Acetic Acid → HCID 178517926, compound

HRID 1246780Notes

Reaction equation

HRID 1246780 reaction equation
[Cl:1][C:2]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:3]=1[C:4]([NH:6][C:7]1[C:8](Cl)=[N:9][CH:10]=[N:11][C:12]=1[NH:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)=O.C(O)(=[O:29])C>>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([N:13]2[C:4]([C:3]3[CH:22]=[CH:23][C:24]([Cl:26])=[CH:25][C:2]=3[Cl:1])=[N:6][C:7]3[C:12]2=[N:11][CH:10]=[N:9][C:8]=3[OH:29])=[CH:15][CH:16]=1

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 219058382,4-dichloro-N-[4-chloro-6-(4-chlorophenylamino)-pyrimidin-5-yl]-benzamide

Product 1

HCID 178517926HCID 178517926, compound

Conditions

Temperature
0 °C

Procedure

A suspension of 2,4-dichloro-N-[4-chloro-6-(4-chlorophenylamino)-pyrimidin-5-yl]-benzamide I-(1A-1)b (48 g, 0.11 mol) in acetic acid (1 l) was heated to reflux for 7 hours. The reaction mixture was cooled to 0° C., the product (colorless needles) was collected by vacuum filtration, and the solid was washed with additional acetic acid, ethyl acetate, and then ether. The product was dried overnight under high vacuum to afford the title compound I-(1A-1)c (32 g, 73%) as a colorless, fluffy solid. The mother liquor was concentrated under reduced pressure and the solid crystallized from methanol to provide additional material (16 g) as a colorless solid: mp 314–315° C.; +ESI MS (M+1) 391.3; 1H NMR: (400 MHz, CD3OD): δ 8.06 (s, 1H), 7.61 (d, J=8.3 Hz, 1H), 7.52 (d, J=2.1 Hz, 1H), 7.48–7.41 (m, 3H), 7.31 (d, J=8.7 Hz, 2H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 7 hours
  3. filtrationthe product (colorless needles) was collected by vacuum filtration
  4. washthe solid was washed with additional acetic acid, ethyl acetate
  5. customThe product was dried overnight under high vacuum

Sources & evidence

ORD record
ord-2be57018ab9445e19bced6fe32f5320b
Source dataset
uspto-grants-2006_10
Patent number
US07129239B2

Reaction notes

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