Sodium Azide → HCID 20274398, compound

HRID 371133Notes

Reaction equation

HRID 371133 reaction equation
[CH3:1][N:2]1[CH2:10][C:9]2([C:11]3[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=3)[CH:4]([CH:5]3[CH2:18][CH:8]2[CH:7]=[CH:6]3)[CH2:3]1.N([O-])=O.[Na+].[N-:23]=[N+:24]=[N-].[Na+]>O>[N:17]([C:14]1[CH:15]=[CH:16][C:11]([C:9]23[CH:8]4[CH2:18][CH:5]([CH2:6][CH2:7]4)[CH:4]2[CH2:3][N:2]([CH3:1])[CH2:10]3)=[CH:12][CH:13]=1)=[N+:23]=[N-:24]

Participants

5

Reactant 3

HCID 33557Sodium AzideHCID 13519524HCID 13519524, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 20274398HCID 20274398, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

A 200 mg portion of 4-(1,2,3,4,7,7a-hexahydro-2-methyl-4,7-methano-3aH-isoindol-3a-yl)benzenamine was suspended in 35 ml of water, the pH was adjusted to 1.6 and the solution was cooled to 5° C. A 59 mg portion of sodium nitrite was added and the mixture was stirred for one hour at 5° C. A 54 mg portion of sodium azide was added, the cooling bath removed and the reaction protected from light for one hour. Still protected from light, the mixture was diluted with ether, made basic with sodium hydroxide and evaporated at reduced pressure, giving 210 mg of the desired product as a brown oil.

Workup

  1. customthe cooling bath removed
  2. waitthe reaction protected from light for one hour
  3. additionthe mixture was diluted with ether
  4. customevaporated at reduced pressure

Sources & evidence

ORD record
ord-41d7d23dae484892b47c226473870b02
Source dataset
uspto-grants-1985_07
Patent number
US04529736

Reaction notes

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