Ethyl 3-amino-4,4,4-trifluorocrotonate → 3-(4-chloro-5-ethylsulfonylamino-2-fluorophenyl)-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione

HRID 36802

反応式

HRID 36802 の反応式
[NH2:1]/[C:2](/[C:9]([F:12])([F:11])[F:10])=[CH:3]\[C:4]([O:6]CC)=O.C[O-].[Na+].[Cl:16][C:17]1[C:28]([NH:29][S:30]([CH2:33][CH3:34])(=[O:32])=[O:31])=[CH:27][C:20]([NH:21][C:22](=O)[O:23]CC)=[C:19]([F:35])[CH:18]=1>CN(C)C=O>[Cl:16][C:17]1[C:28]([NH:29][S:30]([CH2:33][CH3:34])(=[O:32])=[O:31])=[CH:27][C:20]([N:21]2[C:4](=[O:6])[CH:3]=[C:2]([C:9]([F:10])([F:11])[F:12])[NH:1][C:22]2=[O:23])=[C:19]([F:35])[CH:18]=1

参加物

5

反応物 3

HCID 5702529Ethyl 3-amino-4,4,4-trifluorocrotonateHCID 10903456Ethyl 4-chloro-5-ethylsulfonylamino-2-fluorocarbanilateHCID 10942334Sodium Methoxide

生成物 1

HCID 111124793-(4-chloro-5-ethylsulfonylamino-2-fluorophenyl)-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione収率 77%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
5 °C

実験手順

1.06 g (5.77 mmol) of ethyl 3-amino-4,4,4-trifluorocrotonate was dissolved in 6.2 ml of N,N-dimethylformamide and 0.82 g (14.4 mmol) of sodium methoxide was added thereto. The reaction mixture was cooled to not higher than 5° C. after 10 minutes, and 1.56 g (4.81 mmol) of ethyl 4-chloro-5-ethylsulfonylamino-2-fluorocarbanilate was added thereto. The resultant mixture was heated to 110° C. and reacted for 4 hours. After the reaction was completed, N,N-dimethylformamide was distilled off and the resultant product was dissolved in water. The thus-obtained solution was washed with diethyl ether 3 times and thereafter concentrated hydrochloric acid was added thereto to pH 2. The precipitated crystals were filtered out, washed with water and dried to obtain 1.54 g of the objective product (yield: 77%) in the form of light yellow crystals.

後処理

  1. customreacted for 4 hours
  2. distillationN,N-dimethylformamide was distilled off
  3. dissolutionthe resultant product was dissolved in water
  4. washThe thus-obtained solution was washed with diethyl ether 3 times
  5. additionconcentrated hydrochloric acid was added
  6. filtrationThe precipitated crystals were filtered out
  7. washwashed with water
  8. customdried

出典と根拠

ORDレコード
ord-dbd92c8c458a4f7abe5413cf41b0ee55
出典データセット
uspto-grants-1995_05
特許番号
US05416236

関連ノート

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