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Hydrochloric Acid → 4-[3-Pentyl-3-(5,5,8,8-Tetramethyl-5,6,7,8-Tetrahydro-Naphthalen-2-yl)-Ureido]-Benzoic Acid

HRID 1760840
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HRID 1760840 반응식
[CH2:1]([N:6]([C:21]1[CH:30]=[CH:29][C:28]2[C:27]([CH3:32])([CH3:31])[CH2:26][CH2:25][C:24]([CH3:34])([CH3:33])[C:23]=2[CH:22]=1)[C:7](=[O:20])[NH:8][C:9]1[CH:19]=[CH:18][C:12]([C:13]([O:15]CC)=[O:14])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH3:5].[OH-].[K+].C1COCC1.Cl>C(O)C.O>[CH2:1]([N:6]([C:21]1[CH:30]=[CH:29][C:28]2[C:27]([CH3:32])([CH3:31])[CH2:26][CH2:25][C:24]([CH3:33])([CH3:34])[C:23]=2[CH:22]=1)[C:7](=[O:20])[NH:8][C:9]1[CH:19]=[CH:18][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH3:5]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 11784539HCID 11784539, 화합물

생성물 1

HCID 101602234-[3-Pentyl-3-(5,5,8,8-Tetramethyl-5,6,7,8-Tetrahydro-Naphthalen-2-yl)-Ureido]-Benzoic Acid수율 83.3%

시약·촉매·용매 2

HCID 702
Ethanol
용매
HCID 962Water용매2회

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온도
45 °C

실험 절차

A solution of ethyl 4-[3-pentyl-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ureido]-benzoate (37) (360 mg, 0.77 mmole) in 10 mL ethanol was treated with 430 mg of potassium hydroxide in 2 mL water. THF (2 mL) was added and the mixture was heated to 45° C. for two hours. The reaction mixture was diluted with 10 mL water, the pH adjusted to 2 with concentrated HCl and then extracted with three 25 mL portions of ethyl acetate. The combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo, to give a pale yellow solid. The product was purified by trituration in pentane and 280 mg of 4-[3-pentyl-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ureido]-benzoic acid (27) were obtained as a white solid. M.P.: 184-186° C.

후처리

  1. extractionextracted with three 25 mL portions of ethyl acetate
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give a pale yellow solid
  6. customThe product was purified by trituration in pentane

출처 및 근거

ORD 기록
ord-15875df89ccc486fb9e16083cb76d2db
출처 데이터셋
uspto-grants-2005_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06844466B2

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