Triethylamine → [4-(1-methyl-1H-tetrazol-5-yl)-phenyl]-carbamic acid phenyl ester

HRID 395370Notes

Reaction equation

HRID 395370 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=2)=[N:5][N:4]=[N:3]1.C(N(CC)CC)C.Cl[C:22]([O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:23].CCOC(C)=O>C1COCC1>[C:25]1([O:24][C:22](=[O:23])[NH:13][C:10]2[CH:11]=[CH:12][C:7]([C:6]3[N:2]([CH3:1])[N:3]=[N:4][N:5]=3)=[CH:8][CH:9]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 15891Phenyl chloroformateHCID 222590184-(1-methyl-1H-1,2,3,4-tetrazol-5-yl)aniline

Product 1

HCID 22973281[4-(1-methyl-1H-tetrazol-5-yl)-phenyl]-carbamic acid phenyl esterYield 29.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(1-Methyl-1H-tetrazol-5-yl)-phenylamine (190 mg, 1.08 mmol, 1 eq.), triethylamine (0.14 ml, 1.08 mmol, 1 eq.), in 10 ml of THF under nitrogen were cooled to 0° C. A 5 ml solution of phenyl chloroformate (0.14 ml, 1.08 mmol, 1 eq.), was added dropwise via an addition funnel. Worked up after 16 hours by adding EtOAc then rinsing 3× with H2O. The organic layer was dried over MgSO4, then stripped to obtain yellow solids which were purified over silica gel in 3:1 hexanes/EtOAc to 100% EtOAc. Obtained 93 mg of white solids as product. Mass Spec, 296 (M+H). NMR (300 MHz, DMSO-d6) δ 10.65 (s, 2H), 7.86 (d, 2H, J=7 Hz), 7.76 (d, 2H, J=7 Hz), 7.44 (t, 2H, J=7Hz), 7.28 (t, 2H, J=7 Hz), 4.18 s, 3H).

Workup

  1. washthen rinsing 3× with H2O
  2. dry with materialThe organic layer was dried over MgSO4
  3. customto obtain yellow solids which
  4. customwere purified over silica gel in 3:1 hexanes/EtOAc to 100% EtOAc

Sources & evidence

ORD record
ord-6f478106846647128b4a08039cc24f0e
Source dataset
uspto-grants-2003_08
Patent number
US06605623B1

Reaction notes

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