Pyridine → Cloransulam-Methyl

HRID 1741264Notes

Reaction equation

HRID 1741264 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[C:3]=1[NH2:12].N1C=CC=CC=1.Cl[S:20]([C:23]1[N:31]=[C:30]2[N:25]([C:26]([O:33][CH2:34][CH3:35])=[N:27][C:28]([F:32])=[CH:29]2)[N:24]=1)(=[O:22])=[O:21]>ClCCl>[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[C:3]=1[NH:12][S:20]([C:23]1[N:31]=[C:30]2[N:25]([C:26]([O:33][CH2:34][CH3:35])=[N:27][C:28]([F:32])=[CH:29]2)[N:24]=1)(=[O:21])=[O:22]

Participants

5

Reactant 3

HCID 1049PyridineHCID 109679322-Chlorosulfonyl-5-ethoxy-7-fluoro[1,2,4]triazolo[1,5-c]pyrimidineHCID 11030511Benzoic acid, 2-amino-3-chloro-, methyl ester

Product 1

HCID 86453Cloransulam-MethylYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
10 °C

Procedure

The same product was obtained in a similar fashion using the N-(2-chloro-6-methoxycarbonylphenyl)-S,S-tetramethylenesulfilimine product mixture of Example 4 as the catalyst. A 9 mL portion of that product was diluted with 75 mL of dichloromethane, the solution was cooled to 10° C., and 9.3 g (50 mmol) of methyl 3-chloroanthranilate and then 4.8 g (60 mmol) of pyridine were added with cooling and stirring. 2-Chlorosulfonyl-7-fluoro-5-ethoxy[1,2,4]triazolo[1,5-c]pyrimidine (15.5 g of 91 percent pure, 50 mmol) was added with cooling to 0-2° C. The reaction was complete in 6 hours and a 90 percent yield of 98 percent purity title compound was obtained on recovery.

Workup

  1. customThe same product was obtained in a similar fashion
  2. temperaturewith cooling
  3. temperaturewith cooling to 0-2° C

Sources & evidence

ORD record
ord-6fc1718668b54829ad450a90d7edf5f4
Source dataset
uspto-grants-1999_10
Patent number
US05973148

Reaction notes

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