Trichloroisocyanuric Acid → HCID 14600677, compound

HRID 1259345Notes

Reaction equation

HRID 1259345 reaction equation
[CH3:1][C:2]1[N:12]=[CH:11][C:10]([CH3:13])=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[Cl:14]N1C(=O)N(Cl)C(=O)N(Cl)C1=O>C(Cl)Cl.C(=O)([O-])[O-].[Na+].[Na+]>[Cl:14][CH2:1][C:2]1[N:12]=[CH:11][C:10]([CH3:13])=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

5

Reactant 2

HCID 6909Trichloroisocyanuric AcidHCID 12356204HCID 12356204, compound

Product 1

HCID 14600677HCID 14600677, compoundYield 109.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 10340Sodium CarbonateSolvent

Procedure

As shown in step 11-ii of Scheme 11, Compound 2035 (354 mg, 1.98 mmol) and 1,3,5-trichloro-1,3,5-triazinane-2,4,6-trione (689 mg, 2.96 mmol) were combined in DCM (1.8 mL). After stirring 18 hours at room temperature, the mixture was diluted with 20 mLs each of saturated sodium carbonate and dichloromethane. The organics were separated, washed with saturated sodium carbonate, washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give ethyl 2-(chloromethyl)-5-methylnicotinate (Compound 2036, 465 mg) as a pale yellow oil: ESMS (M+1) 213.86.

Workup

  1. customThe organics were separated
  2. washwashed with saturated sodium carbonate
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fecf1731e1534e428507e3cbfe96630f
Source dataset
uspto-grants-2013_06
Patent number
US08466288B2

Reaction notes

Loading…