4-Acetamidobenzenesulfonyl azide → Benzyl 5-diazo-1-(3,4-dichlorobenzyl)-4-oxo-4,5,6,7-tetrahydroindole-2-carboxylate

HRID 1596537

Reaction equation

HRID 1596537 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][C:30]=1[Cl:31])[CH2:5][N:6]1[C:14]2[CH2:13][CH2:12][CH:11](C=O)[C:10](=[O:17])[C:9]=2[CH:8]=[C:7]1[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19].C(NC1C=CC(S([N:45]=[N+:46]=[N-])(=O)=O)=CC=1)(=O)C>C(N(CC)CC)C>[N+:45](=[C:11]1[CH2:12][CH2:13][C:14]2[N:6]([CH2:5][C:4]3[CH:28]=[CH:29][C:30]([Cl:31])=[C:2]([Cl:1])[CH:3]=3)[C:7]([C:18]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:19])=[CH:8][C:9]=2[C:10]1=[O:17])=[N-:46]

Participants

4

Reactant 2

HCID 51291854-Acetamidobenzenesulfonyl azideHCID 9846845Benzyl 1-(3,4-dichlorobenzyl)-5-formyl-4-oxo-4,5,6,7-tetrahydroindole-2-carboxylate

Product 1

HCID 21702187Benzyl 5-diazo-1-(3,4-dichlorobenzyl)-4-oxo-4,5,6,7-tetrahydroindole-2-carboxylateYield 62.3%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Triethyl amine (0.36 mL) was added dropwise to a solution of benzyl 1-(3,4-dichlorobenzyl)-5-formyl-4-oxo-4,5,6,7-tetrahydroindole-2-carboxylate (0.5 g) and p-acetamidobenzenesulphonyl azide (305 mg) at room temperature, and stirred for 18 hours to give a brown solution. The solvent was removed in vacuo to afford a brown oil. Purification by column chromatography, using iso-hexane : 20% ethyl acetate as eluent afforded the title compound as a pale yellow solid (0.31 g, 62%), NMR d(CDCl3) 2.80 (2H, t), 3.05 (2H, t), 5.13 (2H, s), 5.57 (2H, s), 6.76 (1H, dd), 7.05 (1H, s), 7.20-7.40 (7H, m); M/z (+) 456, 454 (M+).

Workup

  1. customto give a brown solution
  2. customThe solvent was removed in vacuo
  3. customto afford a brown oil
  4. customPurification by column chromatography

Sources & evidence

ORD record
ord-284bc519df334634806c4a3f05accb08
Source dataset
uspto-grants-2001_09
Patent number
US06291507B1

Linked notes

Loading…