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Dimethylformamide → 1-(2-chloroethyl)-1,4-dihydro-4-[2-(2-thienyl)ethyl]-5H-tetrazol-5-one

HRID 1863031
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HRID 1863031 반응식
CC1C=CC(S(O[CH2:12][CH2:13][C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)(=O)=O)=CC=1.[Cl:19][CH2:20][CH2:21][N:22]1[C:26](=[O:27])[NH:25][N:24]=[N:23]1.C(=O)([O-])[O-].[Na+].[Na+].CN(C)C=O>O>[Cl:19][CH2:20][CH2:21][N:22]1[C:26](=[O:27])[N:25]([CH2:12][CH2:13][C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)[N:24]=[N:23]1
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참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 36820342-Thiopheneethanol tosylateHCID 1358293471-(2-chloroethyl)-1,4-dihydro-5H-tetrazol-5-one

생성물 1

HCID 136767151-(2-chloroethyl)-1,4-dihydro-4-[2-(2-thienyl)ethyl]-5H-tetrazol-5-one수율 46.5%

시약·촉매·용매 1

HCID 962
Water
용매

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온도
70 °C

실험 절차

A mixture of 19.6 parts of [2-(2-thienyl)ethyl] 4-methylbenzenesulfonate, 10 parts of 1-(2-chloroethyl)-1,4-dihydro-5H-tetrazol-5-one, 10 parts of sodium carbonate and 90 parts of N,N-dimethylformamide is stirred and heated overnight at 70° C. The reaction mixture is cooled, 100 parts of water are added and the product is extracted three times with methylbenzene. The combined extracts are dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and petroleumether (70:30 by volume) as eluent. The pure fractions are collected and the eluent is evaporated, yielding 15 parts (46.5%) of 1-(2-chloroethyl)-1,4-dihydro-4-[2-(2-thienyl)ethyl]-5H-tetrazol-5-one as a residue.

후처리

  1. temperatureThe reaction mixture is cooled
  2. extractionthe product is extracted three times with methylbenzene
  3. customThe combined extracts are dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue is purified by column-chromatography over silica gel using
  7. additiona mixture of trichloromethane and petroleumether (70:30 by volume) as eluent
  8. customThe pure fractions are collected
  9. customthe eluent is evaporated

출처 및 근거

ORD 기록
ord-ad396ef9be6d4c6ca56c4eb5415ac18b
출처 데이터셋
uspto-grants-1979_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04167574

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