HCID 59829820, compound → N-(1-methyl-1H-indol-5-yl)-N''-(2,4-bis-benzyloxy-5-bromo-benzylidene)-semicarbazide

HRID 1881368Notes

Reaction equation

HRID 1881368 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([NH:11][NH:12][C:13]([NH2:15])=[O:14])=[CH:8][CH:9]=2)[CH:4]=[CH:3]1.[CH2:16]([O:23][C:24]1[CH:31]=[C:30]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:29]([Br:40])=[CH:28][C:25]=1[CH:26]=O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(O)C>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([NH:11][NH:12][C:13]([N:15]=[CH:26][C:25]3[CH:28]=[C:29]([Br:40])[C:30]([O:32][CH2:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[CH:31][C:24]=3[O:23][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:14])=[CH:8][CH:9]=2)[CH:4]=[CH:3]1

Participants

4

Reactant 2

HCID 59829820HCID 59829820, compoundHCID 68754247N-(1-methyl-1H-indol-5-yl)-semicarbazide

Product 1

HCID 68752992N-(1-methyl-1H-indol-5-yl)-N''-(2,4-bis-benzyloxy-5-bromo-benzylidene)-semicarbazide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A flask was charged with N-(1-methyl-1H-indol-5-yl)-semicarbazide (3.83 g; 18.77 mmol), 2,4-bis-benzyloxy-5-bromobenzaldehyde (7.46 g; 18.77 mmol) and ethanol (100 mL). The reaction was stirred at reflux for one hour, cooled, filtered, washed with ethanol (2×20 mL), and dried under vacuum to give N-(1-methyl-1H-indol-5-yl)-N″-(2,4-bis-benzyloxy-5-bromo-benzylidene)-semicarbazide, which was used crude in the next step.

Workup

  1. temperatureat reflux for one hour
  2. temperaturecooled
  3. filtrationfiltered
  4. washwashed with ethanol (2×20 mL)
  5. customdried under vacuum

Sources & evidence

ORD record
ord-c923dc3c931742589d2850e998df9ed1
Source dataset
uspto-grants-2012_11
Patent number
US08318790B2

Reaction notes

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