Acetic Anhydride → 9-Acetoxy-3,4-diazatricyclo[4,2,1,02,5]nona-3,7-diene

HRID 1981098Notes

Reaction equation

HRID 1981098 reaction equation
[OH:1][CH:2]1[CH:8]2[CH:9]=[CH:10][CH:3]1[CH:4]1[CH:7]2[N:6]=[N:5]1.[C:11](OC(=O)C)(=[O:13])[CH3:12].C(N(CC)CC)C>CCOCC>[C:11]([O:1][CH:2]1[CH:8]2[CH:9]=[CH:10][CH:3]1[CH:4]1[CH:7]2[N:6]=[N:5]1)(=[O:13])[CH3:12]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 70539013HCID 70539013, compound

Product 1

HCID 867400289-Acetoxy-3,4-diazatricyclo[4,2,1,02,5]nona-3,7-diene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

5 parts of 9-hydroxy-3,4-diazatricyclo[4,2,1,02,5 ]nona-3,7-diene, 5 parts of acetic anhydride, 1 part of triethylamine and 100 parts of ether were refluxed for 24 hours, after which the reaction mixture was extracted twice with 50 parts of water, and the organic phase was dried with MgSO4 and evaporated down in a rotary evaporator to give 6.2 parts (95 mole %) of 9-acetoxy-3,4-diazatricyclo[4,2,1,02,5 ]nona-3,7-diene of melting point 58° C.

Workup

  1. extractionafter which the reaction mixture was extracted twice with 50 parts of water
  2. dry with materialthe organic phase was dried with MgSO4
  3. customevaporated down in a rotary evaporator

Sources & evidence

ORD record
ord-37b2695f948348a188a8a1879465d1f0
Source dataset
uspto-grants-1985_04
Patent number
US04512795

Reaction notes

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