Hydrochloric Acid → N-[(Butylamino)carbonyl]-1-methyl-1H-benzotriazole-4-sulfonamide

HRID 1722196Notes

Reaction equation

HRID 1722196 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([S:11]([NH2:14])(=[O:13])=[O:12])[C:5]=2[N:4]=[N:3]1.C(=O)([O-])[O-].[K+].[K+].[CH2:21]([N:25]=[C:26]=[O:27])[CH2:22][CH2:23][CH3:24].Cl>CC(=O)CC>[CH2:21]([NH:25][C:26]([NH:14][S:11]([C:10]1[C:5]2[N:4]=[N:3][N:2]([CH3:1])[C:6]=2[CH:7]=[CH:8][CH:9]=1)(=[O:13])=[O:12])=[O:27])[CH2:22][CH2:23][CH3:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8110Butyl isocyanateHCID 11430Potassium CarbonateHCID 141800401-methyl-1H-1,2,3-benzotriazole-4-sulfonamide

Product 1

HCID 14180041N-[(Butylamino)carbonyl]-1-methyl-1H-benzotriazole-4-sulfonamide

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

To a stirred mixture of 1-methyl-1H-benzotriazole-4-sulfonamide (7.5 g), potassium carbonate (5.1 g), and 2-butanone (250 mL) was added butylisocyanate (3.9 mL) under an inert atmosphere. The reaction was heated at reflux for 15 hours. The cooled reaction mixture was poured into ice (500 mL), acidified with concentrated hydrochloric acid, and extracted with ethyl acetate-tetrahydrofuran. The extracts were dried over magnesium sulfate, filtered, and evaporated. The crude solid was washed with chlorobutane-hexanes and air dried to give 8.65 g of the title compound as a white solid, m.p. 170°-173° C.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 15 hours
  3. customThe cooled reaction mixture
  4. extractionextracted with ethyl acetate-tetrahydrofuran
  5. dry with materialThe extracts were dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. washThe crude solid was washed with chlorobutane-hexanes and air
  9. customdried

Sources & evidence

ORD record
ord-5662fe2a30f648498fbccab134ca10de
Source dataset
uspto-grants-1989_08
Patent number
US04854962

Reaction notes

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