1-Adamantanecarbonyl chloride → HCID 13559530, compound

HRID 638592Notes

Reaction equation

HRID 638592 reaction equation
[C:1]1([C:7]2[N:12]3[N:13]=[N:14][N:15]=[C:11]3[N:10]3[N:16]=[CH:17][N:18]=[C:9]3[C:8]=2[CH2:19][CH2:20][OH:21])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:22]12([C:32](Cl)=[O:33])[CH2:31][CH:26]3[CH2:27][CH:28]([CH2:30][CH:24]([CH2:25]3)[CH2:23]1)[CH2:29]2>N1C=CC=CC=1.C(Cl)Cl>[C:22]12([C:32]([O:21][CH2:20][CH2:19][C:8]3[C:9]4[N:10]([N:16]=[CH:17][N:18]=4)[C:11]4[N:12]([N:13]=[N:14][N:15]=4)[C:7]=3[C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[O:33])[CH2:29][CH:28]3[CH2:27][CH:26]([CH2:25][CH:24]([CH2:30]3)[CH2:23]1)[CH2:31]2

Participants

5

Reactant 2

HCID 989151-Adamantanecarbonyl chlorideHCID 13559527HCID 13559527, compound

Product 1

HCID 13559530HCID 13559530, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution containing 1.4 g of 5-phenyltetrazolo[1,5-a][1,2,4]triazolo[1,5-c]pyrimidine-6-ethanol (0.005 mole) dissolved in 12 ml of pyridine is added 1.0 g of 1-adamantanecarbonyl chloride (0.005 mole). The reaction mixture is stirred for one hour and then allowed to stand overnight at room temperature. The reaction mixture is evaporated to dryness yielding a residue. The residue is taken up in methylene chloride, extracted with water, dried over sodium sulfate and evaporated to dryness yielding a crude product. The crude product is chromatographed on silica gel to yield 2-(5-phenyltetrazolo[1,5-a][1,2,4]triazolo[1,5-c]pyrimidin-6-yl)ethyl tricyclo[3.3.1.13,7 ]decane-1-carboxylate having the structural formula ##STR25## and the azido tautomer thereof as a white solid having a melting point of 129°-130° C. and the following elemental analysis:

Workup

  1. waitto stand overnight at room temperature
  2. customThe reaction mixture is evaporated to dryness
  3. customyielding a residue
  4. extractionextracted with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated to dryness
  7. customyielding a crude product
  8. customThe crude product is chromatographed on silica gel

Sources & evidence

ORD record
ord-af4605ccb75a4f32817ffe27b47d1898
Source dataset
uspto-grants-1985_12
Patent number
US04562192

Reaction notes

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