Tributylamine → 2-Amino-3-cyclopentylbenzenesulphonyl chloride

HRID 727444Notes

Reaction equation

HRID 727444 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[S:20]([Cl:24])(Cl)(=[O:22])=[O:21].[NH2:25][C:26]1[C:31]([CH:32]2[CH2:36][CH2:35][CH2:34][CH2:33]2)=[CH:30][CH:29]=[CH:28][C:27]=1S(O)(=O)=O.C(N(CCCC)CCCC)CCC>ClCCl>[NH2:25][C:26]1[C:31]([CH:32]2[CH2:36][CH2:35][CH2:34][CH2:33]2)=[CH:30][CH:29]=[CH:28][C:27]=1[S:20]([Cl:24])(=[O:22])=[O:21]

Participants

6

Reactant 4

HCID 7622TributylamineHCID 11776TriphenylphosphineHCID 24648Sulfuryl chlorideHCID 189193792-Amino-3-cyclopentylbenzenesulphonic acid

Product 1

HCID 189316682-Amino-3-cyclopentylbenzenesulphonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 2.42 g (9.2 mmol) of triphenylphosphine in 5 ml of dichloromethane is added dropwise, at 0° C. under a nitrogen atmosphere, 0.70 ml (8.8 mmol) of sulphuryl chloride. The reaction medium is left stirring for 10 minutes at 0° C., followed by addition over 5 minutes of a solution containing 1.06 g (4.4 mmol) of 2-amino-3-cyclopentylbenzenesulphonic acid and 1.04 ml of tributylamine in 3 ml of dichloromethane. The mixture is brought to room temperature and is left at this temperature for 2 hours, then it is purified by chromatography on a column of silica gel, eluting with a dichloromethane/pentane mixture (1:1).

Workup

  1. waitThe reaction medium is left
  2. additionfollowed by addition over 5 minutes of a solution
  3. customis brought to room temperature
  4. waitis left at this temperature for 2 hours
  5. customit is purified by chromatography on a column of silica gel
  6. washeluting with a dichloromethane/pentane mixture (1:1)

Sources & evidence

ORD record
ord-114a4385bd95441d847043f2381166c0
Source dataset
uspto-grants-1998_01
Patent number
US05712393

Reaction notes

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