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

HRID 35254

Reaction equation

HRID 35254 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-f211f03e53b04a2a9cb7041bab37de39
Source dataset
uspto-grants-1988_08
Patent number
US04766120

Linked notes

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