1,2-Ethanediamine, N1,N1-bis(1-methylethyl)- → 4-(2-Diisopropylaminoethylamino)benzenesulfonic acid 2-aminobenzothiazol-6-yl ester

HRID 1867976Notes

Reaction equation

HRID 1867976 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][S:12]([C:15]3[CH:20]=[CH:19][C:18](F)=[CH:17][CH:16]=3)(=[O:14])=[O:13])[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH:22]([N:25]([CH:29]([CH3:31])[CH3:30])[CH2:26][CH2:27][NH2:28])([CH3:24])[CH3:23]>CN1C(=O)CCC1.C(OCC)(=O)C>[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][S:12]([C:15]3[CH:20]=[CH:19][C:18]([NH:28][CH2:27][CH2:26][N:25]([CH:29]([CH3:31])[CH3:30])[CH:22]([CH3:24])[CH3:23])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

5

Reactant 2

HCID 84591,2-Ethanediamine, N1,N1-bis(1-methylethyl)-HCID 579808144-Fluorobenzenesulfonic acid 2-aminobenzothiazol-6-yl ester2×

Product 1

HCID 579808584-(2-Diisopropylaminoethylamino)benzenesulfonic acid 2-aminobenzothiazol-6-yl esterYield 99.1%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 4-fluorobenzenesulfonic acid 2-aminobenzothiazol-6-yl ester (intermediate 16) (100 mg, 0.225 mmol) and N,N-diisopropylethylenediamine (395 μl, 2.25 mmol) in 5 ml of NMP is heated at 150° C. by microwave using an “Emrys™ Optimizer” machine for 20 minutes. The crude reaction product is taken up in 50 ml of ethyl acetate and the resulting solution is washed with 5 times 50 ml of water. After separation of the phases by settling, the organic phase is dried over sodium sulfate, filtered and evaporated under reduced pressure to give 100 mg of 4-(2-diisopropylaminoethylamino)benzenesulfonic acid 2-aminobenzothiazol-6-yl ester.

Workup

  1. customfor 20 minutes
  2. customThe crude reaction product
  3. washthe resulting solution is washed with 5 times 50 ml of water
  4. customAfter separation of the phases
  5. dry with materialthe organic phase is dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-f610471f86664f0d8ae9a74b2c62612b
Source dataset
uspto-grants-2009_12
Patent number
US07632952B2

Reaction notes

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