Water → HCID 178431809, compound

HRID 329215Notes

Reaction equation

HRID 329215 reaction equation
[C:1]12([S:11][CH2:12][CH2:13][N:14]([N:20]=O)[C@H:15]([C:17]([OH:19])=[O:18])[CH3:16])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.O>C(OC(=O)C)(=O)C>[C:1]12([S:11][CH2:12][CH2:13][N+:14]3[N-:20][O:19][C:17](=[O:18])[C:15]=3[CH3:16])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

4

Reactant 2

HCID 962WaterHCID 53941456HCID 53941456, compound

Product 1

HCID 178431809HCID 178431809, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

The N-[2-(1-adamantylthio)ethyl]-N-nitrosoalanine prepared in Example 6 is dissolved in 163 parts of acetic anhydride, then allowed to stand at room temperature for 24 hours. The solution is heated briefly to 65° on a steam bath and allowed to cool to room temperature. Then the solution is added to 1000 parts of water and stirred for 3 hours. The solid which forms is collected by filtration, washed successively with water, and saturated sodium bicarbonate and water, and dried. Recrystallization of the solid from methylene chloride-ether affords pure 3-[2-(1-adamantylthio)ethyl] 4-methylsydnone, melting at about 92°-93° and represented by the following structural formula ##STR8##

Workup

  1. temperatureThe solution is heated briefly to 65° on a steam bath
  2. filtrationThe solid which forms is collected by filtration
  3. washwashed successively with water, and saturated sodium bicarbonate and water
  4. customdried
  5. customRecrystallization of the solid from methylene chloride-ether

Sources & evidence

ORD record
ord-6ca336583f0b48bd898da954d3a53f41
Source dataset
uspto-grants-1977_04
Patent number
US04020079

Reaction notes

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