Pyridine → HCID 178522026, compound

HRID 1492446Notes

Reaction equation

HRID 1492446 reaction equation
[NH:1]1[C:5]([C:6]2[CH:7]=[C:8]([NH2:12])[CH:9]=[CH:10][CH:11]=2)=[N:4][N:3]=[N:2]1.N1C=CC=CC=1.Cl[C:20]([O:22][C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=1)=[O:21]>C(#N)C.CN(C)C=O>[NH:4]1[C:5]([C:6]2[CH:7]=[C:8]([NH:12][C:20](=[O:21])[O:22][C:23]3[CH:24]=[CH:25][C:26]([N+:29]([O-:31])=[O:30])=[CH:27][CH:28]=3)[CH:9]=[CH:10][CH:11]=2)=[N:1][N:2]=[N:3]1

Participants

6

Reactant 3

HCID 1049PyridineHCID 821294-Nitrophenyl chloroformateHCID 178507542HCID 178507542, compound

Product 1

HCID 178522026HCID 178522026, compoundYield 77.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of [3-(1H-tetrazol-5-yl)phenyl]amine (0.97 g, 0.006 mol) in acetonitrile (25 mL), dimethylformamide (3 mL) and pyridine (0.97 mL, 0.95 g, 0.012 mol) under argon at 0° was treated with p-nitrophenyl chloroformate (1.21 g, 0.006 mol) and was stirred at room temperature overnight The reaction mixture was concentrated in vacuo and an effort was made to partition the remaining oil between ethyl acetate and 1M HCl, resulting in separation of a pink solid insoluble in either phase. The solid was sintered off and the organic layer was dried over magnesium sulfate, concentrated in vacuo to give additional product The two crops were combined, triturated with wet ether and dried in vacuo to yield 1.52 g of 3-(1H-tetrazol-5-yl)phenylcarbamic acid, 4-nitrophenyl ester, m.p. 186°-188° C. TLC, silica gel, EtOAc/MeOH/HOAc (20:1:.2), Rf =0.65; M.S. (M+H)+ at 327, M.W. 326. This material was used without further purification.

Workup

  1. concentrationwas concentrated in vacuo
  2. customto partition the remaining oil between ethyl acetate and 1M HCl
  3. customresulting in separation of a pink solid insoluble in either phase
  4. dry with materialthe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto give additional product The two crops
  7. customtriturated with wet ether
  8. customdried in vacuo

Sources & evidence

ORD record
ord-d612f2eb1a5f47fcb8dbe0ea229465b2
Source dataset
uspto-grants-1994_12
Patent number
US05374643

Reaction notes

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