Triethylamine hydrochloride → HCID 178507674, compound

HRID 555904Notes

Reaction equation

HRID 555904 reaction equation
[NH2:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[N-:11]=[N+:12]=[N-:13].[Na+].Cl.C(N(CC)CC)C>C1(C)C=CC=CC=1>[Cl:10][C:8]1[CH:7]=[CH:6][C:3]([C:4]2[NH:13][N:12]=[N:11][N:5]=2)=[C:2]([CH:9]=1)[NH2:1]

Participants

5

Reactant 3

HCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 170059Benzonitrile, 2-amino-4-chloro-

Product 1

HCID 178507674HCID 178507674, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

2-Amino-4-chlorobenzonitrile (1000 mg, 6.6 mmol), sodium azide (555 mg, 8.5 mmol) and triethylamine hydrochloride (1175 mg, 8.5 mmol) were taken up in 15 mL of toluene. The suspension was heated to 100° C. overnight. After cooling, the reaction mixture was washed 3 times with 5 mL portions of water. The combined aqueous fractions were acidified with concentrated hydrochloric acid. The desired 5-Chloro-2-(1H-tetrazol-5-yl)aniline precipitated from aqueous solution and was isolated by filtration (1090 mg, 85% yield). 1H NMR (500 MHz, DMSO-d6) δ 7.73 (d, 1H), 6.97 (d, 1H), 6.74 (dd, 1H); MS (electrospray) m/z 196 (M+H).

Workup

  1. temperatureAfter cooling
  2. washthe reaction mixture was washed 3 times with 5 mL portions of water
  3. customThe desired 5-Chloro-2-(1H-tetrazol-5-yl)aniline precipitated from aqueous solution
  4. customwas isolated by filtration (1090 mg, 85% yield)

Sources & evidence

ORD record
ord-064814c5c4b64f52a2767612f605a137
Source dataset
uspto-grants-2011_11
Patent number
US08053454B2

Reaction notes

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