Hydrochloric Acid → HCID 178479021, compound

HRID 1527461Notes

Reaction equation

HRID 1527461 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Br:10])[CH:9]=1)[C:5]#[N:6].[ClH:11].C(N(CC)CC)C.[N-:19]=[N+:20]=[N-:21].[Na+]>C1(C)C=CC=CC=1.C(Cl)Cl.CO>[ClH:11].[Br:10][C:8]1[CH:9]=[C:2]([NH2:1])[CH:3]=[C:4]([C:5]2[NH:21][N:20]=[N:19][N:6]=2)[CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 33557Sodium AzideHCID 534069613-Amino-5-bromobenzonitrile

Product 1

HCID 178479021HCID 178479021, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3-amino-5-bromo-benzonitrile (200 mg, 1.02 mmol) in toluene (2 mL) was added 6N HCl (0.220 mL, 1.32 mmol), triethylamine (0.184 mL, 1.32 mmol) and sodium azide (86.0 mg, 1.32 mmol). The reaction mixture was stirred at 100° C. for 30 min in a microwave apparatus (Personal Chemistry, Biotage), and after cooling to RT was then diluted with CH2Cl2/MeOH (4:1) and washed with 10 mL of water. The organic phase was discarded, and the water phase was acidified to pH=1 by adding 12N HCl. The aqueous layer was freeze-dried overnight to afford the title compound as a yellowish solid. MS (LC/MS): 239.3 [M+H]+; tR (HPLC conditions c): 3.23 min.

Workup

  1. temperatureafter cooling to RT
  2. washwashed with 10 mL of water
  3. additionby adding 12N HCl
  4. customThe aqueous layer was freeze-dried overnight

Sources & evidence

ORD record
ord-ca5f76a0149243ca8e63daef952db057
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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