Semicarbazide → 862574-66-1

HRID 408485Notes

Reaction equation

HRID 408485 reaction equation
[NH2:1][NH:2][C:3]([NH2:5])=[O:4].[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][C:14](O)=O>P(Cl)(Cl)(Cl)=O>[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][C:14]1[O:4][C:3]([NH2:5])=[N:2][N:1]=1

Participants

4

Reactant 2

HCID 5196SemicarbazideHCID 17124o-Chlorophenylacetic acid

Product 1

HCID 18070416862574-66-1

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

Semicarbazide (9.0 g, 120 mmol) was slowly added to a solution of (2-chlorophenyl)acetic acid (10. g, 60 mmol) in phosphorus oxychloride (50 mL). The mixture was stirred at room temperature for 16 hours and then poured into crushed ice (500 g). A viscous solid was decanted from the aqueous layer and then the aqueous layer was adjusted to pH 4 to 5 with sodium hydroxide (50% aqueous solution). The resulting precipitate was filtered and then washed with sodium carbonate (10% aqueous solution, 100 mL) to give the product as a white solid. (5.9 g, 28 mmol, 47%). ESI-MS m/z calc. 209.0. found; 210.1 (M+1)+ 1H NMR (DMSO) δ 7.44-7.30 (m, 4H), 6.88 (s, 2H), 4.13 (s, 2H).

Workup

  1. additionpoured
  2. customA viscous solid was decanted from the aqueous layer
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with sodium carbonate (10% aqueous solution, 100 mL)

Sources & evidence

ORD record
ord-78f6e4b4c819463d94dc748a83eee5f9
Source dataset
uspto-grants-2014_06
Patent number
US08759335B2

Reaction notes

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