Acetic Acid → 1-thioureido-1H-pyrrole-2-carboxamide

HRID 1685966노트

반응식

HRID 1685966 반응식
C([NH:9][C:10](=[S:20])[NH:11][N:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[C:17]([NH2:19])=[O:18])(=O)C1C=CC=CC=1.C([O-])([O-])=O.[K+].[K+].CO.C(O)(=O)C>O.CC(C)=O>[NH:11]([N:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[C:17]([NH2:19])=[O:18])[C:10]([NH2:9])=[S:20]

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 887MethanolHCID 11430Potassium CarbonateHCID 100626351-(((Benzoylamino)thioxomethyl)amino)-1H-pyrrole-2-carboxamide

생성물 1

HCID 104650001-thioureido-1H-pyrrole-2-carboxamide수율 79%

시약·촉매·용매 2

HCID 180Acetone용매HCID 962Water용매

실험 절차

Compound 1A (2.2 g, 7.6 mmol) was treated with a solution of K2CO3 (2.0 g, 14.8 mmol) in water (9 mL) at ambient temperature. Methyl alcohol (70 mL) and acetone (70 mL) were added and the mixture was heated to reflux for 18 hours. The reaction was cooled to ambient temperature and treated with acetic acid (2.0 mL, 35 mmol), and then concentrated to approximately 30 mL. The resulting suspension was cooled to 0° C. and the product was recovered by vacuum filtration to afford 1B (1.1 g, 79%). HPLC tR=0.405 min (YMC S5 Combiscreen ODS 4.6×50 mm, 10-90% aqueous methanol containing 0.2% H3PO4, 4 min gradient, monitored at 254 nm). 1H NMR (400 MHz, DMSO-d6) δ 10.4 (s, 1H), 8.13 (br s, 2H), 7.31 (br s, 1H), 7.10 (br s, 1H), 6.88 (t, 1H, J=2.0 Hz), 6.75 (dd, 1H, J=1.6, 4.0 Hz), 6.05 (t, 1H, J=3.6 Hz).

후처리

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 18 hours
  3. concentrationconcentrated to approximately 30 mL
  4. temperatureThe resulting suspension was cooled to 0° C.
  5. filtrationthe product was recovered by vacuum filtration

출처 및 근거

ORD 기록
ord-547bede71ccb4eb18ee166d62bdbd407
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08148523B2

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