Bicarbonate Ion → HCID 178508998, compound

HRID 1272499Notes

Reaction equation

HRID 1272499 reaction equation
[NH2:1][C:2]1[C:9]([Br:10])=[CH:8][C:7]([N+:11]([O-:13])=[O:12])=[CH:6][C:3]=1[C:4]#[N:5].[NH2:14][C:15](N)=[O:16].C(=O)(O)[O-]>>[NH2:5][C:4]1[C:3]2[C:2](=[C:9]([Br:10])[CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[CH:6]=2)[N:1]=[C:15]([OH:16])[N:14]=1

Participants

4

Reactant 3

HCID 769Bicarbonate IonHCID 1176UreaHCID 871732-Amino-3-bromo-5-nitrobenzonitrile

Product 1

HCID 178508998HCID 178508998, compoundYield 89.4%

Procedure

2-Amino-3-bromo-5-nitro-benzonitrile (1.9003 g, 7.85 mmol) was heated with urea (1.8862 g, 31.4 mmol) at 180–185° C. for 3 hrs. The cooled mixture was powered and treated with bicarbonate solution, filtered and washed with water. The solid was the collected and washed with ethanol, ether, and used for the next step reaction without further purification. 2.0 g product was obtained. Yield 89%; 1H NMR (500 MHz, DMSO-d6): δ 8.44455–8.45011(d, J=2.78 Hz, 1H), 8.87071–8.87544(d, J=2.365 Hz, 1H), 9.39866–9.40333(d, J=2.335 Hz, 1H), 9.50740–9.51282(d, J=2.71 Hz, 1H); ESI-MS: 285, 287 (M++1)

Workup

  1. filtrationfiltered
  2. washwashed with water
  3. customcollected
  4. washwashed with ethanol, ether
  5. customused for the next step reaction without further purification

Sources & evidence

ORD record
ord-c2ff07cdef1f45b3b5b185a9e4d860fd
Source dataset
uspto-grants-2007_04
Patent number
US07208493B2

Reaction notes

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