Benzylamine → 6-(3,5-Dichloro-phenylsulphonylamino)-naphthalene-1-carboxylic acid-benzylamide

HRID 1697270Notes

Reaction equation

HRID 1697270 reaction equation
C(N(C(C)C)CC)(C)C.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.F[B-](F)(F)F.[Cl:32][C:33]1[CH:34]=[C:35]([S:40]([NH:43][C:44]2[CH:45]=[C:46]3[C:51](=[CH:52][CH:53]=2)[C:50]([C:54]([OH:56])=O)=[CH:49][CH:48]=[CH:47]3)(=[O:42])=[O:41])[CH:36]=[C:37]([Cl:39])[CH:38]=1.[CH2:57]([NH2:64])[C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1>CN(C)C=O.O>[CH2:57]([NH:64][C:54]([C:50]1[C:51]2[C:46](=[CH:45][C:44]([NH:43][S:40]([C:35]3[CH:34]=[C:33]([Cl:32])[CH:38]=[C:37]([Cl:39])[CH:36]=3)(=[O:42])=[O:41])=[CH:53][CH:52]=2)[CH:47]=[CH:48][CH:49]=1)=[O:56])[C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1

Participants

7

Reactant 4

HCID 7504BenzylamineHCID 81531Diisopropylethylamine2×HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 584969666-(3,5-Dichloro-phenylsulphonylamino)-naphthalene-1-carboxylic acid

Product 1

HCID 595341116-(3,5-Dichloro-phenylsulphonylamino)-naphthalene-1-carboxylic acid-benzylamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1.50 ml diisopropylethylamine and 2.81 g O-(benzotriazol-1-yl)-1,1,3,3-tetramethyluronium-tetrafluoroborate are added to 3.47 g 6-(3,5-dichloro-phenylsulphonylamino)-naphthalene-1-carboxylic acid in 15 ml N,N-dimethylformamide. The reaction mixture is stirred for 15 minutes at ambient temperature, then 0.97 ml benzylamine and 1.50 ml diisopropylethylamine are added and the mixture is stirred for a further two hours at ambient temperature. For working up the reaction mixture is mixed with water and extracted with ethyl acetate. The combined organic extracts are washed with 1N hydrochloric acid, 1N sodium hydroxide solution and saturated sodium chloride solution, dried on magnesium sulphate and evaporated down. The foam-like flask residue is stirred overnight with cyclohexane/ethyl acetate and the resulting crystalline precipitate is suction filtered, washed with cyclohexane and dried.

Workup

  1. stirringthe mixture is stirred for a further two hours at ambient temperature
  2. extractionextracted with ethyl acetate
  3. washThe combined organic extracts are washed with 1N hydrochloric acid, 1N sodium hydroxide solution and saturated sodium chloride solution
  4. customdried on magnesium sulphate
  5. customevaporated down
  6. stirringThe foam-like flask residue is stirred overnight with cyclohexane/ethyl acetate
  7. filtrationfiltered
  8. washwashed with cyclohexane
  9. customdried

Sources & evidence

ORD record
ord-544393e52cff49298097fa50c485f823
Source dataset
uspto-grants-2012_04
Patent number
US08163911B2

Reaction notes

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