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Sulfuric Acid → 4-Phenyl-2-nitrobenzenediazonium hydrogen sulfate

HRID 48564
Notes
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Reaction equation

HRID 48564 reaction equation
[S:1](=[O:5])(=[O:4])([OH:3])[OH:2].[N:6]([O-])=O.[Na+].[N+:10]([C:13]1[CH:14]=[C:15]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:16]=[CH:17][C:18]=1[NH2:19])([O-:12])=[O:11].C(OCC)C>C(O)(=O)C>[S:1]([O-:5])([OH:4])(=[O:3])=[O:2].[C:20]1([C:15]2[CH:16]=[CH:17][C:18]([N+:19]#[N:6])=[C:13]([N+:10]([O-:12])=[O:11])[CH:14]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 3283Diethyl EtherHCID 77705[1,1'-Biphenyl]-4-amine, 3-nitro-2×HCID 23668193Sodium Nitrite2×

Product 1

HCID 858226914-Phenyl-2-nitrobenzenediazonium hydrogen sulfate

Reagents, catalysts & solvents 1

HCID 176
Acetic Acid
Solvent

Conditions

Temperature
20 °C

Procedure

To 70 mL of sulfuric acid at 10° C. is added portionwise sodium nitrite (7 g, 0.1 mol). The reaction mixture is warmed to 20° C. to dissolve all the sodium nitrite and then cooled to 15° C. To the reaction mixture is added over 30 minutes a suspension of 3-nitro-4-amino-1,1′-biphenyl (7.33 g, 0.034 mol), prepared in (B) above, in 60 mL of acetic acid. The reaction mixture is stirred for one hour at 10° C. and then to the reaction mixture is added 500 mL of diethyl ether. An exotherm occurs. The mixture is stirred for one hour. The solid formed is removed by filtration behind a safety shield and washed with diethyl ether to give 16.2 g of the title compound as a yellow solid. The solid is dried for 1.5 hours at 20° C. under vacuum and stored in a freezer in a polyethylene container until later use. Analysis: IR (nujol) v 1650 (N═N), 2250 (N2+) cm−1.

Workup

  1. temperaturecooled to 15° C
  2. additionTo the reaction mixture is added over 30 minutes
  3. stirringThe mixture is stirred for one hour
  4. customThe solid formed
  5. customis removed by filtration behind a safety shield
  6. washwashed with diethyl ether

Sources & evidence

ORD record
ord-b81197e5af114fd2834c650810480dc0
Source dataset
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06703510B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes