4-Chlorobenzenesulfonyl chloride → HCID 12945833, compound

HRID 2248135Notes

Reaction equation

HRID 2248135 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][C:5]1[CH:15]=[CH:14][C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:7][CH:6]=1.C(N(CC)CC)C.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1>C(Cl)Cl>[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([S:30]([NH:2][CH2:3][CH2:4][C:5]2[CH:15]=[CH:14][C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:7][CH:6]=2)(=[O:32])=[O:31])=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 12945885Ethyl 4-(2-aminoethyl)benzoate--hydrogen chloride (1/1)

Product 1

HCID 12945833HCID 12945833, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A suspension of 11.5 g. (50 mMol) ethyl 4-(2-aminoethyl)-benzoate hydrochloride (J.A.C.S., 65, 2281, 2284/1943) and 12.65 g. (125 mMol) triethylamine in 150 ml. methylene chloride is stirred for 30 minutes at ambient temperature, cooled to 0° C. and a solution of 11.55 g. (50 mMol) 4-chlorobenzenesulphonic acid chloride in 50 ml. methylene chloride slowly added dropwise thereto. After ending of the reaction, the reaction mixture is extracted twice with dilute hydrochloric acid, washed with water and the organic phase then dried over anhydrous sodium sulphate. After evaporation of the solvent, there are obtained 11.4 g. (62% of theory) of colourless crystals; m.p. 88° C., after recrystallisation from ethanol.

Workup

  1. additionA suspension of 11.5 g
  2. customAfter ending of the reaction
  3. extractionthe reaction mixture is extracted twice with dilute hydrochloric acid
  4. washwashed with water
  5. dry with materialthe organic phase then dried over anhydrous sodium sulphate
  6. customAfter evaporation of the solvent, there
  7. customare obtained 11.4 g
  8. customm.p. 88° C., after recrystallisation from ethanol

Sources & evidence

ORD record
ord-20f7319ad1254366986843ffb124f9a1
Source dataset
uspto-grants-1991_08
Patent number
US05037990

Reaction notes

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