Triethylamine → Benzenesulfonamide

HRID 648138Notes

Reaction equation

HRID 648138 reaction equation
Br.CC1C=C(C)N2OC(=N)N=C2[N:4]=1.[N+]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[S:23](Cl)(=[O:25])=[O:24])([O-])=O.C(N(CC)CC)C>C(Cl)Cl>[C:18]1([S:23]([NH2:4])(=[O:25])=[O:24])[CH:19]=[CH:20][CH:21]=[CH:22][CH:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 155402-Nitrobenzenesulfonyl chlorideHCID 20482042HCID 20482042, compound

Product 1

HCID 7370Benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred suspension of 1.6 g of 5,7-dimethyl-2H-[1,2,4]oxadiazolo[2,3-a]pyrimidine-2-imine hydrobromide and 1.4 g of o-nitrobenzenesulfonyl chloride in 60 ml of anhydrous methylene chloride at 0° C. is added a solution of 1.0 g of triethylamine in 10 ml of anhydrous methylene chloride dropwise. After addition, the mixture is stirred at 0° C. for 0.5 hour and then at ambient temperature for 2.5 hours. The mixture is then filtered. The filtrate is concentrated under reduced pressure and then column chromatographied (silica gel) to yield 2-nitro-N-[5,7-dimethyl-2H-[1,2,4)oxadiazolo(2,3-a)pyrimidin-2-ylidene]]benzenesulfonamide.

Workup

  1. additionAfter addition
  2. waitat ambient temperature for 2.5 hours
  3. filtrationThe mixture is then filtered
  4. concentrationThe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-70191a4921224ef99499c824c2184016
Source dataset
uspto-grants-1983_10
Patent number
US04411690

Reaction notes

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