Hydrochloric Acid → Benzenesulfonyl azide

HRID 1248968

Reaction equation

HRID 1248968 reaction equation
[C:1]1([S:7]([NH:10][NH2:11])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.C(O)(=O)CCCCCCCCCCCCCCCCC.[NH2:33]CCS(O)(=O)=O.N([O-])=O.[Na+].N([O-])=O>O>[C:1]1([S:7]([N:10]=[N+:11]=[N-:33])(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 946NitriteHCID 1123TaurineHCID 5281Stearic AcidHCID 65723Benzenesulfonyl hydrazideHCID 23668193Sodium Nitrite2×

Product 1

HCID 555606Benzenesulfonyl azide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

25 g of benzenesulphonohydrazide, 200 ml of water, 20 ml of 10N hydrochloric acid and 1.25 g of a product of condensing stearic acid with taurine are stirred for 30 minutes. 60 g of ice are added, and 34 ml of an aqueous sodium nitrite solution containing 30 g of sodium nitrite in 100 ml of solution are then added dropwise in the course of about 30 minutes. The batch is stirred for 30 minutes, an excess of nitrite being maintained. The nitrite excess is then destroyed with a small amount of sulphamic acid, and excess acid is neutralised with about 5 ml of 10N sodium hydroxide solution (pH 4-7). An emulsion of benzenesulphonyl azide is obtained.

Workup

  1. additionare then added dropwise in the course of about 30 minutes
  2. stirringThe batch is stirred for 30 minutes
  3. customThe nitrite excess is then destroyed with a small amount of sulphamic acid, and excess acid

Sources & evidence

ORD record
ord-b45bee630a1c46ea9ae5b840ee2739d9
Source dataset
uspto-grants-1986_12
Patent number
US04628082

Linked notes

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