Sodium Azide → HCID 21445477, compound

HRID 597561Notes

Reaction equation

HRID 597561 reaction equation
Br[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12](=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[Cl:19])=[O:4].[N-:21]=[N+:22]=[N-:23].[Na+].[OH-].C([N+](C)(C)C)C1C=CC=CC=1>CO>[N:21]([C:2]1[C:3](=[O:4])[NH:5][C:6]2[C:7]([C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[Cl:19])=[CH:8][CH:9]=[CH:10][CH:11]=2)=[N+:22]=[N-:23]

Participants

5

Reactant 3

HCID 33557Sodium AzideHCID 66854Benzyltrimethylammonium hydroxideHCID 21445470HCID 21445470, compound

Product 1

HCID 21445477HCID 21445477, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a warm solution of 5.0 g. of 2-bromo-2'-(2-chlorobenzoyl)acetanilide in 100 ml. of methanol was added 1.8 g. of sodium azide. The solution was heated to reflux for 15 minutes. On addition of 0.77 ml. of a 35 percent solution of benzyltrimethylammonium hydroxide in methanol, and standing at room temperature overnight, 1.8 g. of pure (tlc) 3-azido-4-(2-chlorophenyl)carbostyril crystallized and was collected and washed with methanol. On recrystallization from dimethylformamide-methanol, pale yellow needles were obtained, having a melting point of 152°-155° dec.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 15 minutes
  3. additionOn addition of 0.77 ml
  4. customof pure (tlc) 3-azido-4-(2-chlorophenyl)carbostyril crystallized
  5. customwas collected
  6. washwashed with methanol
  7. customOn recrystallization from dimethylformamide-methanol
  8. custompale yellow needles were obtained

Sources & evidence

ORD record
ord-6c269efb126a42bda265b28101620ec3
Source dataset
uspto-grants-1977_03
Patent number
US04014883

Reaction notes

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