Crotononitrile → Evandamine

HRID 745758Notes

Reaction equation

HRID 745758 reaction equation
Cl.[NH:2]([C:4]1[S:5][C:6]2[CH2:12][CH2:11][CH2:10][CH2:9][C:7]=2[N:8]=1)[NH2:3].CC[O-].[Na+].[Na].[C:18](#[N:22])/[CH:19]=[CH:20]/[CH3:21]>O.C(O)C>[NH2:22][C:18]1[CH2:19][CH:20]([CH3:21])[N:2]([C:4]2[S:5][C:6]3[CH2:12][CH2:11][CH2:10][CH2:9][C:7]=3[N:8]=2)[N:3]=1

Participants

7

Reactant 4

HCID 637921CrotononitrileHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 23312423HCID 23312423, compound

Product 1

HCID 3038554EvandamineYield 60.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

20 g of 2-hydrazino-4,5,6,7-tetrahyro-benzothiazole hydrochloride are added to a sodium ethylate solution of 5.7 g of sodium and 250 ml of ethanol and the mixture is stirred at room temperature for 10 minutes. 5.5 g of crotononitrile are then added dropwise and the mixture is boiled under reflux for 5 hours. After cooling, the ethanol is stripped off in vacuo and the residue is taken up in water. The insoluble material is filtered off and washed thoroughly with water, acetone and ether in succession. After drying, 11.8 g of beige crystals of 3-amino-5-methyl-1-(4,5,6,7-tetrahydro-benzothiazolyl)-2-pyrazoline of melting point 247°-249° C. are obtained.

Workup

  1. temperatureunder reflux for 5 hours
  2. temperatureAfter cooling
  3. filtrationThe insoluble material is filtered off
  4. washwashed thoroughly with water, acetone and ether in succession
  5. customAfter drying

Sources & evidence

ORD record
ord-49c689f31b734893be0dda0216d25fa6
Source dataset
uspto-grants-1986_07
Patent number
US04600722

Reaction notes

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