Phenethylamine → 4-methyl-N-phenethyl-1,2,3-thiadiazole-5-carboxamide

HRID 361600

반응식

HRID 361600 반응식
[CH3:1][C:2]1[N:3]=[N:4][S:5][C:6]=1[C:7]([OH:9])=O.C1(N=C=NC2CCCCC2)CCCCC1.[CH2:25]([NH2:33])[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>ClCCl.CN(C)C1C=CN=CC=1>[CH2:25]([NH:33][C:7]([C:6]1[S:5][N:4]=[N:3][C:2]=1[CH3:1])=[O:9])[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

참가 물질

6

반응물 3

HCID 1001PhenethylamineHCID 10868DicyclohexylcarbodiimideHCID 13819924-Methyl-1,2,3-thiadiazole-5-carboxylic acid

생성물 1

HCID 75767364-methyl-N-phenethyl-1,2,3-thiadiazole-5-carboxamide수율 94.6%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

반응 조건

온도
5 °C

실험 절차

A suspension of 9.65 g of 4-methyl-[1,2,3]thiadiazol-5-carboxylic acid in 70 ml of dichlormethane was cooled to 5° C. while stirring, treated with 0.15 g of 4-dimethylamino-pyridine and subsequently with 13.8 g of N,N'-dicyclohexyl-carbodiimide at such a rate that the internal temperature <10° C. could be maintained. After completion of the addition, the mixture was cooled to 5° C. and 8.92 g of phenethylamine were added at such a rate that the internal temperature of <37° C. could be maintained. After completion of the addition, the mixture was stirred for a further 1 h., then the precipitate was filtered off under suction, rinsed well with dichloromethane and the filtrate was evaporated. The residual yellow oil was subjected to chromatography on silica gel with hexane/ethyl acetate 50:50. There were obtained 15.66 g (92%) of 4-methyl-[1,2,3]thiadiazole-5-carboxylic acid phenethylamide as a colorless crystallizate of m.p. 64°-68° C. Recrystallization of a sample from tert.-butyl methyl ether gave colorless crystals of m.p. 64.5°-66° C.

후처리

  1. temperaturecould be maintained
  2. additionAfter completion of the addition
  3. temperaturethe mixture was cooled to 5° C.
  4. temperaturecould be maintained
  5. additionAfter completion of the addition
  6. stirringthe mixture was stirred for a further 1 h.
  7. filtrationthe precipitate was filtered off under suction
  8. washrinsed well with dichloromethane
  9. customthe filtrate was evaporated

출처 및 근거

ORD 기록
ord-eef205f0552743a184c7c6b5967655c8
출처 데이터셋
uspto-grants-1999_02
특허 번호
US05866583

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