4-Nitrobenzenesulfonyl chloride → HCID 22326749, compound

HRID 495373Notes

Reaction equation

HRID 495373 reaction equation
C(N(CC)CC)C.[CH:8]1([NH2:12])[CH2:11][CH2:10][CH2:9]1.[N+:13]([C:16]1[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1)([O-:15])=[O:14]>C(Cl)Cl>[CH:8]1([NH:12][S:22]([C:19]2[CH:18]=[CH:17][C:16]([N+:13]([O-:15])=[O:14])=[CH:21][CH:20]=2)(=[O:23])=[O:24])[CH2:11][CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 75645Cyclobutylamine

Product 1

HCID 22326749HCID 22326749, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A stirred solution of triethylamine (7.8 ml, 0.056 mol) and cyclobutylamine (4.8 ml, 0.056 mol) in DCM (100 ml) was cooled in an ice/water bath. A solution of 4-nitrobenzene sulphonyl chloride (11.3 g, 0.05 mol) in DCM (100 ml) was added dropwise. The reaction was stirred for one hour the cooling bath was removed and the mixture stirred for further 3 hours. The reaction mixture was washed with 1M hydrochloric acid (80 ml), water (50 ml) and then brine. The volatiles were evaporated to give the title compound (11.79 g). NMR: 1.50 (m, 2H), 1.75 (m, 2H), 1.9 (m, 2H), 3.70 (m, 1H), 8.00 (1, 2H), 8.30 (d, 1H), 8.40 (d, 2H); m/z: 256.

Workup

  1. customwas removed
  2. stirringthe mixture stirred for further 3 hours
  3. washThe reaction mixture was washed with 1M hydrochloric acid (80 ml), water (50 ml)
  4. customThe volatiles were evaporated

Sources & evidence

ORD record
ord-bd2293ba5fb24de9af1d318ada07764e
Source dataset
uspto-grants-2005_09
Patent number
US06939872B2

Reaction notes

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