Ammonia → 2-acetamido-N-(4-nitrophenyl)benzamide

HRID 547546

反応式

HRID 547546 の反応式
N[C:2]1[CH:19]=[CH:18][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=2)=[O:7])=[CH:4][CH:3]=1.NC1N=C(C)[CH:24]=[C:23](Cl)[N:22]=1.Cl.N.C([O:33]CCO)C>C(OCC)(=O)C.CO.O>[C:23]([NH:22][C:18]1[CH:19]=[CH:2][CH:3]=[CH:4][C:5]=1[C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=1)=[O:7])(=[O:33])[CH3:24]

参加物

9

反応物 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 8076Glycol monoethyl etherHCID 218102-Amino-4-chloro-6-methylpyrimidineHCID 30155604-Amino-4'-nitrobenzanilide

生成物 1

HCID 33533142-acetamido-N-(4-nitrophenyl)benzamide

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
20 °C

実験手順

4-Amino-N-(4-nitrophenyl)benzamide (C1) (730 mg, 2.84 mmol) and 4-chloro-6-methyl-2-pyrimidinylamine (A8) (416 mg, 2.84 mmol) were dissolved in warm 2-ethoxyethanol (20 mL), two drops c.HCl was then added to the reaction mixture was refluxed for 40 min. by which time TLC and MS showed the completion of the reaction. The reaction mixture was diluted with ethyl acetate and cooled to 20° C. The resulting precipitate was filtered and washed with more EtOAc to give a solid product. This was suspended in MeOH and basified with aqueous NH3 and diluted with water. The resulting precipitate was filtered and dried to give C2 (671 mg). The filtrate was concentrated to give a further 276 mg of C2 (92% overall): mp (MeOH)>300° C.; 1H NMR [(CD3)2SO] δ10.59 (s, 1 H, NH), 9.37 (s, 1 H, NH), 8.27-8.24 (m, 2 H, ArH), 8.09-8.06 (m, 2 H, ArH), 8.05-7.90 (m, 4 H, ArH), 6.25 (s, 2 H, NH2), 5.96 (s, 1 H, ArH), 2.16 (s, 3 H, CH3); Mass APCI+ 365.

後処理

  1. temperaturewas refluxed for 40 min. by which time TLC and MS
  2. customthe completion of the reaction
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with more EtOAc
  5. customto give a solid product
  6. filtrationThe resulting precipitate was filtered
  7. customdried

出典と根拠

ORDレコード
ord-1b7779d2ba8a4cf8aadb7468986f4d11
出典データセット
uspto-grants-2011_05
特許番号
US07939546B2

関連ノート

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