Cyanogen Bromide → N-[3-(2-Amino-3-propyl-3,4-dihydro-quinazoline-6-sulfinyl)-phenyl]-benzenesulfonamide

HRID 390285Notes

Reaction equation

HRID 390285 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:10]2[CH:11]=[C:12]([NH:16][S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)(=[O:19])=[O:18])[CH:13]=[CH:14][CH:15]=2)=[O:9])=[CH:4][C:3]=1[CH2:26][NH:27][CH2:28][CH2:29][CH3:30].[N:31]#[C:32]Br>C(O)C>[NH2:31][C:32]1[N:27]([CH2:28][CH2:29][CH3:30])[CH2:26][C:3]2[C:2](=[CH:7][CH:6]=[C:5]([S:8]([C:10]3[CH:11]=[C:12]([NH:16][S:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)(=[O:19])=[O:18])[CH:13]=[CH:14][CH:15]=3)=[O:9])[CH:4]=2)[N:1]=1

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 58625094N-[3-(4-Amino-3-propylaminomethyl-benzenesulfinyl)-phenyl]-benzenesulfonamide

Product 1

HCID 58625174N-[3-(2-Amino-3-propyl-3,4-dihydro-quinazoline-6-sulfinyl)-phenyl]-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of N-[3-(4-amino-3-propylaminomethyl-benzenesulfinyl)-phenyl]-benzenesulfonamide (0.00090 mol) and cyanogen bromide (0.00094 mol) in ethanol (30 mL) was stirred overnight at room temperature, and then the solvent was evaporated. The residue was triturated under diisopropyl ether, and the solids were filtered off. The residue was converted into the free base with a NaOH solution. The mixture was extracted with CH2Cl2, but the product stayed in the aqueous layer so the mixture was desalted with NaCl to yield an oil. The solvent was decanted, and the remaining oil was triturated under CH3CN. The resulting solids were filtered off, washed with diisopropyl ether, and dried to yield the title compound as a solid.

Workup

  1. customthe solvent was evaporated
  2. customThe residue was triturated under diisopropyl ether
  3. filtrationthe solids were filtered off
  4. extractionThe mixture was extracted with CH2Cl2
  5. customto yield an oil
  6. customThe solvent was decanted
  7. customthe remaining oil was triturated under CH3CN
  8. filtrationThe resulting solids were filtered off
  9. washwashed with diisopropyl ether
  10. customdried

Sources & evidence

ORD record
ord-8915edc289384c13b26ce840e1368503
Source dataset
uspto-grants-2013_02
Patent number
US08383637B2

Reaction notes

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