Hydrochloric Acid → HCID 19832761, compound
Reaction equation
ONC1C=CC=CC=1C1N=NN(C)N=1.ON[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23]1[N:27]([CH3:28])[N:26]=[N:25][N:24]=1.N([O-])=O.[Na+].[S:33](=[O:35])=[O:34].[ClH:36]>O.C(O)(=O)C>[Cl:36][S:33]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23]1[N:27]([CH3:28])[N:26]=[N:25][N:24]=1)(=[O:35])=[O:34]Participants
Conditions
- Temperature
- 31 °C
Procedure
To 5 g of a mixture of 5-(2-hydroxylaminophenyl)-2-methyl-2H-tetrazole and 5-(2-hydroxyaminophenyl)-1-methyl-1H-tetrazole dissolved in 12 mL of 37% hydrochloric acid and 5 mL of acetic acid was added with stirring 2.3 g of sodium nitrite dissolved in 10 mL of water at -5° to 5° C. After one hour this solution was added, at 0°-5° C., portionwise to a mixture of 25 mL of acetic acid, 0.5 g of cupric chloride and 5 mL of liquified sulfur dioxide. After the addition was completed the cooling bath was removed and the reaction mixture was allowed to warm to 31° C. whereupon the cooling bath was reapplied and the stirring was continued until two and one half hours after completion of the addition. The mixture was then poured into ice and worked up as described in Example 1 except that the desired methylene chloride solution was concentrated in vacuo to yield an oil which solidified. This product, (3.28 g) which was a mixture of the desired sulfonylchlorides, was of sufficient purity for the preparation of the sulfonamides of Example 4.
Workup
- additionAfter the addition
- customwas removed
- waitthe stirring was continued until two and one half hours
- additionafter completion of the addition
- additionThe mixture was then poured into ice
- concentrationwas concentrated in vacuo
- customto yield an oil which
Sources & evidence
- ORD record
- ord-64aa463a48c4422b8828879b9bbb96f7
- Source dataset
- uspto-grants-1988_05
- Patent number
- US04746353
Reaction notes
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