Hydrochloric Acid → Phenyl 3-ethyl-5-(1-methyl-1H-tetraazol-5-yl)phenylcarbamate

HRID 1592346Notes

Reaction equation

HRID 1592346 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([CH:7]=[C:8]([C:10]2[N:14]([CH3:15])[N:13]=[N:12][N:11]=2)[CH:9]=1)[NH2:6])[CH3:2].N1C(C)=CC=CC=1C.Cl[C:25]([O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:26].Cl>C1COCC1.C(OCC)(=O)C>[CH2:1]([C:3]1[CH:4]=[C:5]([NH:6][C:25](=[O:26])[O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:7]=[C:8]([C:10]2[N:14]([CH3:15])[N:13]=[N:12][N:11]=2)[CH:9]=1)[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 79372,6-LutidineHCID 15891Phenyl chloroformateHCID 222526943-Ethyl-5-(1-methyl-1H-tetrazol-5-yl)aniline

Product 1

HCID 22252693Phenyl 3-ethyl-5-(1-methyl-1H-tetraazol-5-yl)phenylcarbamateYield 97.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

3-Ethyl-5-(1-methyl-1H-tetraazol-5-yl)aniline (3.83 g, 19 mmol, 1 equiv.), was dissolved in THF at 25° C. under nitrogen then 2,6-lutidine (Aldrich, 2.17 ml, 19 mmol, 1 equiv.) was added. Cooled the reaction to 0° C. Added a THF solution of phenyl chloroformate (2.36 ml, 19 mmol, 1 equiv.) dropwise via an addition funnel. Worked up after 1 hour by adding ethyl acetate and 0.1 N HCl. Separated the layers and rinsed the organic layer twice more with 0.1 N HCl and once with brine. The organic layer was dried over MgSO4 then stripped in vacuo to give 6.00 g of tan solids as product. NMR (300 MHz, CDCl3) δ 7.86 (s, 1H), 7.50-7.30 (m, 5H), 7.30-7.10 (m, 3H), 4.17 (s, 3H), 2.71 (q, 2H, J=7 Hz), 1.27 (t, 3H, J=7 Hz).

Workup

  1. temperatureCooled
  2. customthe reaction to 0° C
  3. customSeparated the layers
  4. washrinsed the organic layer twice more with 0.1 N HCl
  5. dry with materialThe organic layer was dried over MgSO4

Sources & evidence

ORD record
ord-2488d87f63564059a6c88267dd936efe
Source dataset
uspto-grants-2007_11
Patent number
US07291744B2

Reaction notes

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