4-Chlorobenzenesulfonyl chloride → HCID 14989644, compound

HRID 1199682Notes

Reaction equation

HRID 1199682 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH2:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])=[N:17][CH:18]=1>N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:12][C:13]2[CH:14]=[CH:15][C:16]([CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])=[N:17][CH:18]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 14989641HCID 14989641, compound

Product 1

HCID 14989644HCID 14989644, compoundYield 63.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-Chlorobenzenesulphonyl chloride (1.09 g, 5.15 mmole) was added portionwise over 10 minutes to a solution of 5-(5-aminopyrid-2-yl)pentanoic acid (1.00 g, 5.15 mmole) in pyridine (15 ml). The resulting solution was stirred for 18 hours when the solvent was removed and the residue was dissolved in dilute sodium hydroxide solution (30 ml). This solution was extracted with ethyl acetate (4×50 ml) the extracts being discarded. The aqueous layer was acidified (pH 3) and extracted with ethyl acetate (4×100 ml). The combined ethyl acetate extracts were dried over magnesium sulphate, evaporated to dryness and the residue was recrystallised from acetonitrile to give the title compound (1.21 g) as a pale yellow solid. m.p. 145°-147° C.

Workup

  1. customwas removed
  2. dissolutionthe residue was dissolved in dilute sodium hydroxide solution (30 ml)
  3. extractionThis solution was extracted with ethyl acetate (4×50 ml) the extracts
  4. extractionextracted with ethyl acetate (4×100 ml)
  5. dry with materialThe combined ethyl acetate extracts were dried over magnesium sulphate
  6. customevaporated to dryness
  7. customthe residue was recrystallised from acetonitrile

Sources & evidence

ORD record
ord-30e03d0f4c6d4e65960ce6a27d42fd14
Source dataset
uspto-grants-1990_02
Patent number
US04902698

Reaction notes

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