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Bromoacetic Acid → 5-[3,5-Bis(1,1-dimethyl-ethyl)-4-hydroxyphenyl]-1,3,4-thiadiazole-2-yl[thio]acetic acid

HRID 466062
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HRID 466062 반응식
[OH-].[Na+].[CH3:3][C:4]([C:7]1[CH:8]=[C:9]([C:18]2[S:22][C:21](=[S:23])[NH:20][N:19]=2)[CH:10]=[C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:12]=1[OH:13])([CH3:6])[CH3:5].Br[CH2:25][C:26]([OH:28])=[O:27]>CO>[CH3:6][C:4]([C:7]1[CH:8]=[C:9]([C:18]2[S:22][C:21]([S:23][CH2:25][C:26]([OH:28])=[O:27])=[N:20][N:19]=2)[CH:10]=[C:11]([C:14]([CH3:15])([CH3:16])[CH3:17])[C:12]=1[OH:13])([CH3:3])[CH3:5]
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참가 물질

5

반응물 3

HCID 6227Bromoacetic AcidHCID 14798Sodium HydroxideHCID 30370185-(3,5-Di-tert-butyl-4-hydroxyphenyl)-1,3,4-thiadiazole-2(3H)-thione

생성물 1

HCID 1360083465-[3,5-Bis(1,1-dimethyl-ethyl)-4-hydroxyphenyl]-1,3,4-thiadiazole-2-yl[thio]acetic acid

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Aqueous 1M NaOH (12.4 ml, 0.0124 mole) is added to 0° C. solution of 5-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-1,3,4-thiadiazole-2(3H)-thione (2.0 g, 0.0062 mole) in methanol (20 ml). This is followed by addition of 2-bromoacetic acid (0.95 g, 0.0068 mole) in one portion. The resulting mixture is allowed to stir four hours with periodic warming. The solution is concentrated in vacuo and the residue is partitioned between ether and water. The layers are separated and the aqueous phase is made acidic with aqueous 6M HCl. The aqueous layer is extracted with 1:1 ethyl acetate/ether (2×). The combined organic layers are washed with saturated aqueous NaCl, and dried over MgSO4. Filtration and concentration in vacuo provides a solid which is recrystallized from ethyl acetate/hexane to give 1.6 g (2.4 g theor., 68%) of [[5-[3,5-bis(1,1-dimethyl-ethyl)-4-hydroxyphenyl]-1,3,4-thiadiazole-2-yl[thio]acetic acid, mp 187.5° C.

후처리

  1. concentrationThe solution is concentrated in vacuo
  2. customthe residue is partitioned between ether and water
  3. customThe layers are separated
  4. extractionThe aqueous layer is extracted with 1:1 ethyl acetate/ether (2×)
  5. washThe combined organic layers are washed with saturated aqueous NaCl
  6. dry with materialdried over MgSO4
  7. filtrationFiltration and concentration in vacuo
  8. customprovides a solid which
  9. customis recrystallized from ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-4fb952043afc4d5a8fc656d7b410d806
출처 데이터셋
uspto-grants-1992_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05155122

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