Dimethylformamide → HCID 86687364, compound

HRID 1473308Notes

Reaction equation

C[N:2]1[C:6]([C:7]2[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[CH:9][C:8]=2[C:17]2[CH:26]=[CH:25][CH:24]=[C:23]3[C:18]=2[CH:19]=[CH:20][C:21]([S:27]([OH:30])(=[O:29])=[O:28])=[CH:22]3)=[CH:5][CH:4]=[N:3]1.S(Cl)(Cl)=O.[CH3:35]N(C=O)C>>[CH3:35][N:3]1[CH:4]=[CH:5][C:6]([C:7]2[CH:12]=[C:11]([C:13]([F:16])([F:14])[F:15])[CH:10]=[CH:9][C:8]=2[C:17]2[CH:26]=[CH:25][CH:24]=[C:23]3[C:18]=2[CH:19]=[CH:20][C:21]([S:27]([OH:30])(=[O:28])=[O:29])=[CH:22]3)=[N:2]1

Participants

Reactant 3

HCID 6228Dimethylformamide

HCID 24386Thionyl Chloride

HCID 86687365HCID 86687365, compound

Product 1

HCID 86687364HCID 86687364, compound

Procedure

To a solution of 5-(2-(1-methyl-1H-pyrazol-5-yl)-4-(trifluoromethyl)phenyl)naphthalene-2-sulfonic acid (from Step 2) (0.093 g, 0.214 mmol) in DMF (0.428 mL) was added thionyl chloride (0.031 mL, 0.428 mmol) at 0° C. After 20 minutes LC/MS indicated that the sulfonic acid starting material was converted to the desired product. The reaction mixture was then transferred to a separatory funnel containing water and DCM. The layers were separated and the organic layer was washed twice with water. The resulting organic layer was dried with MgSO4, filtered and concentrated to an oil. m/z (ESI, +ve ion) 450.9 (M+1).

Sources & evidence

ORD record: ord-bf75cf8264d44d1eb915eb7c88b8ffcd
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09012443B2

Reaction notes

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