2-Chloro-p-toluidine-5-sulfonic acid → HCID 10452330, compound

HRID 2111963Notes

Reaction equation

HRID 2111963 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1C(O)=O.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:20])C=CC=CC=1.C([N:32]([CH2:35]C)CC)C.[NH2:37][C:38]1[CH:43]=[C:42]([Cl:44])[C:41]([CH3:45])=[CH:40][C:39]=1[S:46]([OH:49])(=[O:48])=[O:47]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Cl:44][C:42]1[C:41]([CH3:45])=[CH:40][C:39]([S:46]([OH:49])(=[O:48])=[O:47])=[C:38]([NH:37][C:35]([NH:32][C:2]2[NH:1][C:9]3[C:4]([CH:3]=2)=[CH:5][CH:6]=[CH:7][CH:8]=3)=[O:20])[CH:43]=1

Participants

7

Reactant 4

HCID 69352-Chloro-p-toluidine-5-sulfonic acidHCID 8471Triethylamine2×HCID 72899Indole-2-carboxylic acidHCID 199401P,P-Diphenylphosphinic azide

Product 1

HCID 10452330HCID 10452330, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Indole-2-carboxylic acid (1.29 g, 8.0 mmol) was suspended in 20 ml dry toluene and diphenyl-phosphoryl azide (2.64 g, 9.6 mmol) added. Triethylamine (0.816 g, 8.0 mmol) was then added drop-wise and the mixture stirred at room temperature for 0.5 hour. The solution was heated to 80° C. and the suspension cleared immediately. Then 2-Amino-4-chloro-5-methyl-benzenesulfonic acid (1.661 g, 8.0 mmol) was added and triethylamine (0.816 g, 8.0 mmol. The mixture was stirred for 3 hours at 80° C. and then the reaction mixture was diluted with 200 ml ethyl acetate and washed with saturated aqueous sodium bicarbonate. The organic phase was then extracted 3 times with distilled water. The title compound was precipitated from the aqueous phase with addition of HCl, filtered and recrystallised from ethyl acetate/heptane to yield 1.6 g (53%) of title compound as light purple crystalline solid (m.p. 284-286° C.; decomposition).

Workup

  1. temperatureThe solution was heated to 80° C.
  2. stirringThe mixture was stirred for 3 hours at 80° C.
  3. washwashed with saturated aqueous sodium bicarbonate
  4. extractionThe organic phase was then extracted 3 times with distilled water
  5. customThe title compound was precipitated from the aqueous phase with addition of HCl
  6. filtrationfiltered
  7. customrecrystallised from ethyl acetate/heptane

Sources & evidence

ORD record
ord-af8f590877f848c3ac0b02d83c2ee191
Source dataset
uspto-grants-2009_04
Patent number
US07521480B2

Reaction notes

Loading…