Thionyl Chloride → HCID 59186036, compound

HRID 1671341Notes

Reaction equation

HRID 1671341 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]2[N:17]=[C:16]([CH3:18])[C:15]([C:19]([OH:21])=O)=[C:11]2[O:12][C:13]=1[CH3:14].O=S(Cl)[Cl:24]>>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]2[N:17]=[C:16]([CH3:18])[C:15]([C:19]([Cl:24])=[O:21])=[C:11]2[O:12][C:13]=1[CH3:14]

Participants

3

Reactant 2

HCID 24386Thionyl Chloride2×HCID 59186035HCID 59186035, compound

Product 1

HCID 59186036HCID 59186036, compound

Procedure

A mixture comprising 3-(2,4-dichloro-phenyl)-2,6-dimethyl-pyrazolo[5,1-b]oxazole-7-carboxylic acid (Intermediate IBB) (1 g, 3.08 mmol) and SOCl2 (10 ml, 137 mmol) is heated at reflux for 2 hours. After cooling to room temperature excess SOCl2 is removed under vacuum. The resulting solid is azeotroped with toluene until any remaining SOCl2 is removed to afford the title compound as a solid; 1H NMR (400 MHz, CDCl3) δ 2.48 (s, 3H), 2.53 (s, 3H), 7.48 (q, 1H), 7.52 (q, 1H), 7.62 (d, 1H).

Workup

  1. temperatureat reflux for 2 hours
  2. customis removed under vacuum
  3. customThe resulting solid is azeotroped with toluene until any remaining SOCl2
  4. customis removed

Sources & evidence

ORD record
ord-f225bd60b16748f6b6e66ad2df7926ac
Source dataset
uspto-grants-2011_08
Patent number
US07994203B2

Reaction notes

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