Triethylamine → Benzo[1,2,5]thiadiazole-4-carboxylic acid methoxy-methyl-amide

HRID 747257

反応式

HRID 747257 の反応式
[N:1]1[S:5][N:4]=[C:3]2[C:6]([C:10]([OH:12])=O)=[CH:7][CH:8]=[CH:9][C:2]=12.C(Cl)(=O)C(Cl)=O.Cl.[CH3:20][NH:21][O:22][CH3:23].C(N(CC)CC)C>C1C=CC=CC=1.C(Cl)(Cl)Cl.CN(C=O)C.C(Cl)Cl>[CH3:23][O:22][N:21]([CH3:20])[C:10]([C:6]1[C:3]2=[N:4][S:5][N:1]=[C:2]2[CH:9]=[CH:8][CH:7]=1)=[O:12]

参加物

9

反応物 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27952022,1,3-Benzothiadiazole-4-carboxylic acid

生成物 1

HCID 59749564Benzo[1,2,5]thiadiazole-4-carboxylic acid methoxy-methyl-amide収率 90%

試薬・触媒・溶媒 4

HCID 241Benzene溶媒HCID 6212Chloroform溶媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

A suspension of benzo[1,2,5]thiadiazole-4-carboxylic acid (Intermediate L1) (1.8 g, 9.99 mmol) (commercially available from Maybridge) in benzene (100 mL) was treated with oxalyl chloride (5.1 mL of a 2 M CH2Cl2 solution) and DMF (catalytic amount) at rt for 1 h. The solvent was removed under vacuum and re-suspended in benzene. The mixture was decanted into a flask and concentrated under vacuum. The acid chloride intermediate was dissolved in chloroform (10 mL) and added to a solution of N,O-dimethylhydroxylamine-HCl (1.47 g, 15 mmol) (commercially available from Aldrich) and triethylamine (4 mL, 30 mmol) in chloroform (90 mL) at 0° C. The mixture was stirred at rt for 2 h. The mixture was subjected to a standard aqueous work-up. All solvent was removed under vacuum and the residue was purified by chromatography on silica gel with 50% EtOAc:hexane to give benzo[1,2,5]thiadiazole-4-carboxylic acid methoxy-methyl-amide (Intermediate L2) 2 g (90% over two steps).

後処理

  1. customThe solvent was removed under vacuum
  2. customThe mixture was decanted into a flask
  3. concentrationconcentrated under vacuum
  4. dissolutionThe acid chloride intermediate was dissolved in chloroform (10 mL)
  5. customAll solvent was removed under vacuum
  6. customthe residue was purified by chromatography on silica gel with 50% EtOAc

出典と根拠

ORDレコード
ord-230e8d73e781496aaa1a8724d53153d1
出典データセット
uspto-grants-2008_07
特許番号
US07396849B2

関連ノート

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