Hydrochloric Acid → HCID 24854610, compound

HRID 1660927Notes

Reaction equation

HRID 1660927 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([C:9]2[C:14](Cl)=[C:13]([Cl:16])[N:12]=[C:11]([Cl:17])[N:10]=2)[CH:3]=1.Cl>S1C=CC=C1C([O-])=O.[Cu+].CN1CCCC1=O>[Cl:17][C:11]1[N:12]=[C:13]([Cl:16])[C:14]2[O:8][C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=3[C:9]=2[N:10]=1

Participants

5

Reactant 2

HCID 313Hydrochloric Acid2×HCID 135874460HCID 135874460, compound

Product 1

HCID 24854610HCID 24854610, compoundYield 83.8%

Reagents, catalysts & solvents 2

HCID 11194830Cuprous 2-thiophenecarboxylateCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
100 °C

Procedure

A 10 mL flask was charged with 4-chloro-2-(2,5,6-trichloro-pyrimidin-4-yl)-phenol (75 mg, 0.24 mmol) and N-methylpyrrolidinone (3.0 mL) under a N2 atmosphere. The solution was purged with N2 for 10 min. Copper (I) thiophene-2-carboxylate (60 mg, 0.32 mmol, 1.3 equiv.) was added and the mixture was heated to 100° C. for 2 h. The reaction mixture was cooled to rt and added to aq. HCl (0.1 M, 6.0 mL) slowly and stirred for 15 min. Additional aq. HCl (0.1 M, 3.0 mL) was added and the mixture was stirred for 20 min. The resulting solid was collected by filtration, rinsed with water, and dried to give a tan solid (55 mg, 83%). GC-MS (CI): mass calcd. for C10H3Cl3N2O, 271.9; m/z found, 272.0. 1H NMR (CDCl3): 8.22 (d, J=2.1 Hz, 1H), 7.75 (dd, J=8.9, 2.1 Hz, 1H), 7.69 (d, J=9.0 Hz, 1H).

Workup

  1. customThe solution was purged with N2 for 10 min
  2. temperatureThe reaction mixture was cooled to rt
  3. stirringthe mixture was stirred for 20 min
  4. filtrationThe resulting solid was collected by filtration
  5. washrinsed with water
  6. customdried

Sources & evidence

ORD record
ord-ff2eb87c610e4ea79b1fbd7e5552369f
Source dataset
uspto-grants-2011_10
Patent number
US08030321B2

Reaction notes

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