Triethylamine → HCID 86622289, compound

HRID 1639558Notes

Reaction equation

HRID 1639558 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:14]=1[S:20](Cl)(=[O:22])=[O:21].C(N(CC)CC)C>CC(C)=O>[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:14]=1[S:20]([O:8][C:5]1[CH:6]=[CH:7][C:2]([NH2:1])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1)(=[O:22])=[O:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5221832,6-Dichlorobenzenesulfonylchloride2×HCID 37588824-Amino-3-Nitrophenol

Product 1

HCID 86622289HCID 86622289, compoundYield 44.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 3.14 g of 4-amino-3-nitrophenol in 50 cm3 of acetone are added 5 g of 2,6-dichlorobenzenesulfonyl chloride. The reaction medium is stirred for five minutes and then placed in a bath of ice-water so as not to exceed 30° C. during the addition of 2.9 cm3 of triethylamine. The formation of a precipitate is observed, and the mixture is stirred for twenty-four hours at a temperature in the region of 20° C. 500 mg of 2,6-dichlorobenzenesulfonyl chloride are added and, after stirring for two hours, the insoluble material is filtered off, washed with three times 30 cm3 of acetone and set aside*. The filtrate is evaporated to dryness under reduced pressure (2 kPa) and the residue is taken up in 1 L of dichloromethane and then washed with three times 40 cm3 of water. The organic phase is dried over magnesium sulfate, filtered and evaporated to dryness under reduced pressure (2 kPa). 3.28 g of 4-amino-3-nitrophenyl 2,6-dichlorobenzenesulfonate are obtained in the form of orange crystals, the characteristics of which are as follows:

Workup

  1. stirringthe mixture is stirred for twenty-four hours at a temperature in the region of 20° C
  2. stirringafter stirring for two hours
  3. filtrationthe insoluble material is filtered off
  4. washwashed with three times 30 cm3 of acetone
  5. customThe filtrate is evaporated to dryness under reduced pressure (2 kPa)
  6. washwashed with three times 40 cm3 of water
  7. dry with materialThe organic phase is dried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated to dryness under reduced pressure (2 kPa)

Sources & evidence

ORD record
ord-608f3c22b032416bba5b451b98b3c716
Source dataset
uspto-grants-2012_02
Patent number
US08110571B2

Reaction notes

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