Methyl chloroformate → N-(4-methoxycyclohexyl)-4-(1-methyl-1,2,3,4-tetrazol-5-yl)thio-butyramide

HRID 35254

반응식

HRID 35254 반응식
[CH3:1][N:2]1[C:6]([CH2:7][CH2:8][CH2:9][C:10](O)=[S:11])=[N:5][N:4]=[N:3]1.CN1[CH2:19][CH2:18][O:17][CH2:16]C1.ClC(OC)=O.CO[CH:27]1[CH2:32]CC[CH2:29][CH:28]1[NH2:33]>O.C(Cl)Cl>[CH3:16][O:17][CH:18]1[CH2:19][CH2:29][CH:28]([NH:33][C:10](=[S:11])[CH2:9][CH2:8][CH2:7][C:6]2[N:2]([CH3:1])[N:3]=[N:4][N:5]=2)[CH2:27][CH2:32]1

참가 물질

7

반응물 4

HCID 6586Methyl chloroformateHCID 79724-MethylmorpholineHCID 222508792-Methoxycyclohexan-1-amineHCID 178482013HCID 178482013, 화합물

생성물 1

HCID 53790851N-(4-methoxycyclohexyl)-4-(1-methyl-1,2,3,4-tetrazol-5-yl)thio-butyramide수율 43%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

To methylene chloride (50 ml) are added 4-(1-methyl-1,2,3,4-tetrazol-5-yl)thio-butyric acid (45 mmole) and N-methylmorpholine (50 mmole). To the mixture is added dropwise with stirring methyl chloroformate (50 mmole) with keeping the inner temperature at 10°-20° C. by ice-cooling, and thereafter, the mixture is stirred at room temperature for 30 minutes. To the mixture is added 2-methoxycyclohexylamine (54 mmole), and the mixture is stirred at the same temperature for 4 hours. After the reaction, water is added to the reaction mixture. The organic layer is separated and washed with dilute aqueous sodium hydroxide solution, diluted hydrochloric acid and water in order, and dried over sodium sulfate. Inorganic materials are filtered off, and the mother liquor is concentrated. The resulting residue is subjected to column chromatography (Wakogel C-200, eluting solvent, benzene:chloroform=4:1, V/V) to isolate N-(4-methoxycyclohexyl)-4-(1-methyl-1,2,3,4-tetrazol-5-yl)thio-butyramide (yield: 43%), colorless liquid, nD11 =1.5263.

후처리

  1. customat 10°-20° C.
  2. temperaturecooling
  3. stirringthe mixture is stirred at the same temperature for 4 hours
  4. additionis added to the reaction mixture
  5. customThe organic layer is separated
  6. washwashed with dilute aqueous sodium hydroxide solution, diluted hydrochloric acid and water in order
  7. dry with materialdried over sodium sulfate
  8. filtrationInorganic materials are filtered off
  9. concentrationthe mother liquor is concentrated
  10. washThe resulting residue is subjected to column chromatography (Wakogel C-200, eluting solvent, benzene:chloroform=4:1, V/V)

출처 및 근거

ORD 기록
ord-f211f03e53b04a2a9cb7041bab37de39
출처 데이터셋
uspto-grants-1988_08
특허 번호
US04766120

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