Triethylamine → HCID 11494746, compound

HRID 2301517Notes

Reaction equation

HRID 2301517 reaction equation
[CH2:1]1[O:12][C:11]2[C:3](=[C:4]([CH:8]=[CH:9][CH:10]=2)C(O)=O)[O:2]1.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[C:39]([OH:49])=[C:40]([S:45]([NH2:48])(=[O:47])=[O:46])[C:41]([Cl:44])=[CH:42][CH:43]=1>CN(C)C=O>[Cl:44][C:41]1[CH:42]=[CH:43][C:38]([NH:37][C:35]([NH:32][C:4]2[CH:8]=[CH:9][CH:10]=[C:11]3[O:12][CH2:1][O:2][C:3]=23)=[O:20])=[C:39]([OH:49])[C:40]=1[S:45]([NH2:48])(=[O:47])=[O:46]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 3048321,3-Dioxaindane-4-carboxylic acidHCID 113680593-Amino-6-chloro-2-hydroxy-benzenesulfonamide

Product 1

HCID 11494746HCID 11494746, compoundYield 57.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2,3-(methylenedioxy)benzoic acid (170mg, 1.02mmol), diphenylphosphoryl azide (338 mg, 1.23 mmol) and triethylamine (0.17mL, 1.23 mmol) was stirred at room temperature for 3 days. The mixture was concentrated. To the residue in 1 mL of N,N-dimethylformamide was added 3-amino-6-chloro-2-hydroxybenzenesulfonamide (40 mg, 0.18 mmol). The resulting mixture was stirred at room temperature for 16 hours. Purification by column chromatography on silica gel, eluting with ethyl acetate/hexane (50/50, v/v), gave the desired product (40 mg, 10%). EI-MS (m/z) 386.2, 388.2 (M−).

Workup

  1. concentrationThe mixture was concentrated
  2. stirringThe resulting mixture was stirred at room temperature for 16 hours
  3. customPurification by column chromatography on silica gel
  4. washeluting with ethyl acetate/hexane (50/50

Sources & evidence

ORD record
ord-246a0ea6c31545b5bbbf8a047b2ec896
Source dataset
uspto-grants-2002_12
Patent number
US06500863B1

Reaction notes

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