Hydrochloric Acid → N-[3-methyl-4-(pyrrolidine-1-sulphonyl)-phenyl]-acetamide

HRID 2235050Notes

Reaction equation

HRID 2235050 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11](Cl)(=[O:13])=[O:12])=[C:7]([CH3:15])[CH:6]=1)(=[O:3])[CH3:2].[NH:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1.Cl>[OH-].[Na+].CC(C)=O>[CH3:15][C:7]1[CH:6]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[CH:10]=[CH:9][C:8]=1[S:11]([N:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1)(=[O:13])=[O:12]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 31268PyrrolidineHCID 112838Benzenesulfonyl chloride, 4-(acetylamino)-2-methyl-

Product 1

HCID 67525442N-[3-methyl-4-(pyrrolidine-1-sulphonyl)-phenyl]-acetamide

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 14798Sodium HydroxideSolvent

Procedure

1.45 g of 4-acetylamino-2-methyl-benzenesulphonyl chloride (5.85 mmol) at 0° C. are suspended in 19 ml sodium hydroxide solution (1 M) and then 0.51 ml pyrrolidine (6.47 mmol), dissolved in 9 ml acetone, are added dropwise within half an hour. The solution is heated to ambient temperature overnight and then acidified with hydrochloric acid (2 M). The suspension is extracted twice with ethyl acetate. The combined organic phases are dried over sodium sulphate and evaporated down. A brown oil remains.

Workup

  1. customat 0° C.
  2. additionare added dropwise within half an hour
  3. extractionThe suspension is extracted twice with ethyl acetate
  4. dry with materialThe combined organic phases are dried over sodium sulphate
  5. customevaporated down

Sources & evidence

ORD record
ord-7e09bd2e321d4cdcb55478f28ba847db
Source dataset
uspto-grants-2010_05
Patent number
US07714000B2

Reaction notes

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