Hydrochloric Acid → Cyantraniliprole

HRID 1663512Notes

Reaction equation

HRID 1663512 reaction equation
[Br:1][C:2]1[CH:6]=[C:5]([C:7]([OH:9])=O)[N:4]([C:10]2[C:15]([Cl:16])=[CH:14][CH:13]=[CH:12][N:11]=2)[N:3]=1.[NH2:17][C:18]1[C:27]([CH3:28])=[CH:26][C:25]([C:29]#[N:30])=[CH:24][C:19]=1[C:20]([NH:22][CH3:23])=[O:21].N1C=CC=C(C)C=1.CS(Cl)(=O)=O.Cl>C(#N)C.O>[Br:1][C:2]1[CH:6]=[C:5]([C:7]([NH:17][C:18]2[C:19]([C:20]([NH:22][CH3:23])=[O:21])=[CH:24][C:25]([C:29]#[N:30])=[CH:26][C:27]=2[CH3:28])=[O:9])[N:4]([C:10]2[C:15]([Cl:16])=[CH:14][CH:13]=[CH:12][N:11]=2)[N:3]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 79703-MethylpyridineHCID 31297Methanesulfonyl chlorideHCID 115875353-Bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylic acidHCID 251572822-Amino-5-cyano-N,3-dimethylbenzamide

Product 1

HCID 11578610Cyantraniliprole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
22.5 °C

Procedure

To a mixture of 3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxylic acid (see PCT Patent Publication WO 2003/015519 for a method of preparation) (99.0% purity, 3.03 g, 0.01 mol) and 2-amino-5-cyano-N,3-dimethylbenzamide (prepared by the method of Example 2) (1.99 g, 0.01 mol) in acetonitrile (16 mL) was added 3-picoline (2.92 mL, 0.03 mol). Methanesulfonyl chloride (1.08 mL, 0.014 mol) was added dropwise to the reaction mixture at 20 to 25° C. After stirring for 3 h, water (7.5 mL) was added dropwise to the reaction mixture while maintaining the temperature between 20 to 25° C. After 15 minutes, concentrated hydrochloric acid (0.5 mL) was added and the reaction mixture was stirred for 1 h at 20 to 25° C. The mixture was filtered and the solids collected were washed with acetonitrile-water (87:13 mixture by volume, 2×2 mL) and then with water (2×2 mL), and then dried under nitrogen to afford the title compound (4.80 g, 92.6% corrected yield based on a water-free assay of 96.6%) as an off-white solid melting at 206-208° C.

Workup

  1. waitAfter 15 minutes
  2. stirringthe reaction mixture was stirred for 1 h at 20 to 25° C
  3. filtrationThe mixture was filtered
  4. customthe solids collected
  5. washwere washed with acetonitrile-water (87:13 mixture by volume, 2×2 mL)
  6. dry with materialwith water (2×2 mL), and then dried under nitrogen

Sources & evidence

ORD record
ord-f007ad562a7a4b868e4d4ce140b93b4e
Source dataset
uspto-grants-2011_10
Patent number
US08034968B2

Reaction notes

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