Dichloromethane → N-[5-bromo-6-chloro-2-(4-cyanophenylamino)-pyrimidin-4-yl]benzamide

HRID 243540

反応式

HRID 243540 の反応式
ClCCl.[Cl:4][C:5]1[N:10]=[C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]#[N:19])=[CH:14][CH:13]=2)[N:8]=[C:7]([NH:20][C:21](=[O:28])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:6]=1.[Br:29]Br.S(S([O-])(=O)=O)([O-])(=O)=O>O.C(O)(=O)C>[Br:29][C:6]1[C:7]([NH:20][C:21](=[O:28])[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[N:8][C:9]([NH:11][C:12]2[CH:13]=[CH:14][C:15]([C:18]#[N:19])=[CH:16][CH:17]=2)=[N:10][C:5]=1[Cl:4]

参加物

7

反応物 4

HCID 6344DichloromethaneHCID 24408BromineHCID 3082075DithionateHCID 71465002N-[6-chloro-2-(4-cyanophenylamino)pyrimidin-4-yl]benzamide

生成物 1

HCID 71465003N-[5-bromo-6-chloro-2-(4-cyanophenylamino)-pyrimidin-4-yl]benzamide

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 962Water溶媒

実験手順

1500 ml of dichloromethane and 150 g of N-[6-chloro-2-(4-cyanophenylamino)pyrimidin-4-yl]benzamide were added to a reaction vessel and to this was added 750 ml of acetic acid and 44.2 mL of liquid bromine solution at 27±3° C. and stirred for 11 hrs. After completion of the reaction, to the reaction mixture was added 375 ml of water under stirring and maintained for 45 mins. To the reaction mixture was further added metabisulphate solution (60 g in 375 ml of water) and stirred further for 30 mins. The solid was filtered and washed with 300 ml of water and suck dried. The wet cake and 1500 ml of water were charged into a clean RB and adjusted pH 9.0±0.5 with 50% potassium carbonate solution. The reaction mass was stirred and filtered; the solid was washed with 150 ml of water followed by 150 ml of dichloromethane. The obtained solid was dried under vacuum at 73±2° C. to yield the title compound.

後処理

  1. customAfter completion of the reaction
  2. stirringunder stirring
  3. temperaturemaintained for 45 mins
  4. stirringstirred further for 30 mins
  5. filtrationThe solid was filtered
  6. washwashed with 300 ml of water and suck
  7. customdried
  8. additionThe wet cake and 1500 ml of water were charged into a clean RB and adjusted pH 9.0±0.5 with 50% potassium carbonate solution
  9. stirringThe reaction mass was stirred
  10. filtrationfiltered
  11. washthe solid was washed with 150 ml of water
  12. customThe obtained solid was dried under vacuum at 73±2° C.

出典と根拠

ORDレコード
ord-1dfb970ae5b64db5b5c2d789f77f1fe8
出典データセット
uspto-grants-2014_02
特許番号
US08653266B2

関連ノート

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