Hydrochloric Acid → HCID 178507474, compound

HRID 1807204Notes

Reaction equation

HRID 1807204 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([Cl:10])[CH:3]=1.[N-:11]=[N+:12]=[N-:13].[Na+].Cl.C(N(CC)CC)C.Cl>C1(C)C=CC=CC=1.O>[Cl:10][C:4]1[CH:3]=[C:2]([NH2:1])[CH:9]=[CH:8][C:5]=1[C:6]1[NH:13][N:12]=[N:11][N:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 887284-Amino-2-chlorobenzonitrile

Product 1

HCID 178507474HCID 178507474, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
115 °C

Procedure

To a stirred solution of 4-amino-2-chloro-benzonitrile (Aldrich, 765 mg, 5 mmol) in toluene (10 mL), sodium azide (423 mg, 6.5 mmol) and triethylamine hydrochloride (895 mg, 6.5 mmol) was added and the mixture was stirred vigorously at 115° C. overnight. The mixture was cooled and poured into water. The aqueous layer was adjusted to PH=5 by the addition of 6 N HCl and the solid formed was filtered and dried. 175 mg,

Workup

  1. temperatureThe mixture was cooled
  2. customthe solid formed
  3. filtrationwas filtered
  4. customdried

Sources & evidence

ORD record
ord-0b4fa804d71c494b887a2b04d4452929
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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