Pyridine → Cloransulam-Methyl

HRID 1741264ノート

反応式

HRID 1741264 の反応式
[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]

参加物

5

反応物 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

生成物 1

HCID 86453Cloransulam-Methyl収率 90%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
10 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-6fc1718668b54829ad450a90d7edf5f4
出典データセット
uspto-grants-1999_10
特許番号
US05973148

反応ノート

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