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Hydrochloric Acid → 3-(4-Methoxyphenyl)-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione

HRID 482439
ノート
印刷プレビュー

反応式

HRID 482439 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]=[C:10]=[O:11])=[CH:5][CH:4]=1.[NH2:12]/[C:13](/[C:20]([F:23])([F:22])[F:21])=[CH:14]\[C:15](OCC)=[O:16].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[C:15](=[O:16])[CH:14]=[C:13]([C:20]([F:23])([F:22])[F:21])[NH:12][C:10]2=[O:11])=[CH:7][CH:8]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 794431-Isocyanato-4-methoxybenzeneHCID 5702529Ethyl 3-amino-4,4,4-trifluorocrotonate

生成物 1

HCID 189810643-(4-Methoxyphenyl)-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione収率 58.8%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

実験手順

A stirred solution of 6.0 grams (0.0268 mole) of 4-methoxyphenyl isocyanate, 5.16 grams (0.028 mole) of ethyl 3-amino-4,4,4-trifluorocrotonate, and 4.45 grams (0.032 mole) of potassium carbonate in 40 mL of N,N-dimethylformamide was heated to 140° C. where it stirred for one hour. After this time, the reaction mixture was poured into 100 mL of 10% aqueous hydrochloric acid. The resulting mixture was stirred for ten minutes and then extracted with three 50 mL portions of ethyl acetate. The combined ethyl acetate extracts were dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to yield a black solid. This black solid was purified by flash chromatography, yielding 4.51 grams of 3-(4-methoxyphenyl)-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione. The NMR spectrum was consistent with the proposed structure.

後処理

  1. stirringThe resulting mixture was stirred for ten minutes
  2. extractionextracted with three 50 mL portions of ethyl acetate
  3. dry with materialThe combined ethyl acetate extracts were dried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customto yield a black solid
  7. customThis black solid was purified by flash chromatography

出典と根拠

ORDレコード
ord-676d0b3c48014df0b0a777ba1824a5dd
出典データセット
uspto-grants-1998_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05798316

反応ノート

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