Thionyl Chloride → HCID 86647609, compound

HRID 1947512Notes

Reaction equation

HRID 1947512 reaction equation
[S:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]1[O:10][C:11]1[CH:12]=[CH:13][C:14]2[O:18][C:17]([C:19](O)=[O:20])=[CH:16][C:15]=2[CH:22]=1.S(Cl)([Cl:25])=O>>[ClH:25].[S:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]1[O:10][C:11]1[CH:12]=[CH:13][C:14]2[O:18][C:17]([C:19]([Cl:25])=[O:20])=[CH:16][C:15]=2[CH:22]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 59577467HCID 59577467, compound

Product 1

HCID 86647609HCID 86647609, compoundYield 98%

Procedure

A mixture of 5-(thiazolo[4,5-b]pyridin-2-yloxy)-benzofuran-2-carboxylic acid (326 mg, 1.04 mmol) and thionyl chloride (10 mL) was heated to reflux for 2 h. The crude mixture was concentrated, re-dissolved in CH2Cl2 and concentrated again to provide the product as a yellow solid (375 mg, 98%). 1H NMR (400 MHz, DMSO-d6): 8.61-8.51 (m, 2H), 7.97 (d, J=2.5, 1H), 7.94-7.86 (m, 1H), 7.74 (s, 1H), 7.68-7.61 (m, 1H), 7.46-7.38 (m, 1H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 h
  3. concentrationThe crude mixture was concentrated
  4. dissolutionre-dissolved in CH2Cl2
  5. concentrationconcentrated again

Sources & evidence

ORD record
ord-001a0e94477a469bb76f8aaf62ec1750
Source dataset
uspto-grants-2013_03
Patent number
US08399465B2

Reaction notes

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