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

HRID 747257

반응식

HRID 747257 반응식
[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]

참가 물질

9

반응물 4

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

생성물 1

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

시약·촉매·용매 4

HCID 241Benzene용매HCID 6212Chloroform용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-230e8d73e781496aaa1a8724d53153d1
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07396849B2

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