Thionyl Chloride → HCID 68526992, compound

HRID 1932504Notes

Reaction equation

HRID 1932504 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][C:29]=1[Cl:30])[C:5]([NH:7][C:8]1[CH:9]=[N:10][C:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]O)=[CH:17][CH:16]=2)=[CH:12][CH:13]=1)=[O:6].S(Cl)([Cl:33])=O>>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][C:29]=1[Cl:30])[C:5]([NH:7][C:8]1[CH:9]=[N:10][C:11]([O:14][C:15]2[CH:16]=[CH:17][C:18]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][Cl:33])=[CH:19][CH:20]=2)=[CH:12][CH:13]=1)=[O:6]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 68525810HCID 68525810, compound

Product 1

HCID 68526992HCID 68526992, compound

Procedure

To 3,4-dichloro-N-{6-[4-(5-hydroxypentyl)-phenoxy]pyridin-3-yl}benzamide (6.83 g, 15.34 mmol) was added thionyl chloride (35 mL). The resulting solution was stirred for 20 minutes at room temperature, followed by stirring for 1 hour at 50° C. Excess thionyl chloride was evaporated, after which to the resulting residue was added ethyl acetate (100 mL). The obtained white powder was filtered, and washed with ethyl acetate, to thereby yield 6.98 g of the title compound.

Workup

  1. stirringby stirring for 1 hour at 50° C
  2. customExcess thionyl chloride was evaporated
  3. additionafter which to the resulting residue was added ethyl acetate (100 mL)
  4. filtrationThe obtained white powder was filtered
  5. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-41d55cc9f7fe48f2add7ab14efc29061
Source dataset
uspto-grants-2012_05
Patent number
US08188277B2

Reaction notes

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