Triethylamine → Benzenesulfonamide

HRID 1657619Notes

Reaction equation

HRID 1657619 reaction equation
Cl.NCC[C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH2:14])(=[O:13])=[O:12])=[CH:7][CH:6]=1.C(N(CC)CC)C.CC1N=CSC=1C(Cl)=O>Cl.O1CCCC1>[C:8]1([S:11]([NH2:14])(=[O:13])=[O:12])[CH:9]=[CH:10][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 123345284-(2-Aminoethyl)benzenesulfonamide hydrochlorideHCID 124702104-Methyl-1,3-thiazole-5-carbonyl chloride

Product 1

HCID 7370Benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 1.18 g. (0.005 mole) of 4-(2-aminoethyl)-benzenesulfonamide hydrochloride [E. Miller et al., Journal of the American Chemical Society, Vol. 62, p. 2099 (1940)] and 1.4 ml. (0.010 mole) of triethylamine in 15 ml. of dry tetrahydrofuran, there was added 805 mg. (0.005 mole) of 4-methyl-5-thiazolecarboxylic acid chloride dissolved in 15 ml. of tetrahydrofuran. The addition caused a slight exothermic reaction to occur, after which the reaction mixture was allowed to stand at ambient temperatures for a period of approximately 16 hours with constant agitation being maintained throughout the entire step. At this point, the spent mixture was poured into 50 ml. of ice water and subsequently acidified with a few drops of 3N aqueous hydrochloric acid. The resulting cream-colored precipitate was then recovered by means of suction filtration, washed well with cold water and thereafter crystallized from acetonitrile (after treatment with activated carbon) to yield 1.8 g (73%) of pure 4-[2-methyl-5-thiazolecarboxamido)ethyl]benzenesulfonamide, m.p. 182°-183°C.

Workup

  1. additionTo a mixture of 1.18 g
  2. additionThe addition
  3. customa slight exothermic reaction
  4. temperaturebeing maintained throughout the entire step
  5. additionAt this point, the spent mixture was poured into 50 ml
  6. filtrationThe resulting cream-colored precipitate was then recovered by means of suction filtration
  7. washwashed well with cold water
  8. customcrystallized from acetonitrile (after treatment with activated carbon)

Sources & evidence

ORD record
ord-1d79dd9c76fe4e71b0e669f3537e9852
Source dataset
uspto-grants-1976_06
Patent number
US03961067

Reaction notes

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