Benzenesulfonyl chloride → N-Quinazolin-8-yl-benzenesulfonamide

HRID 513500Notes

Reaction equation

HRID 513500 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[NH2:11])[CH:4]=[N:3][CH:2]=1.[C:12]1([S:18](Cl)(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[NH:11][S:18]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:20])=[O:19])[CH:4]=[N:3][CH:2]=1

Participants

5

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 11344089Quinazolin-8-amine2×

Product 1

HCID 68183159N-Quinazolin-8-yl-benzenesulfonamideYield 54%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

In a similar fashion using route 14 general procedure 27, quinazolin-8-ylamine (Intermediate 480) (60 mg, 0.41 mmol), benzene sulfonyl chloride (94 mg, 0.53 mmol), DMAP (cat.) and pyridine (1 ml) at 150° C. for 2.5 h, gave title compound (30 mg, 54%) after purification by column chromatography with DCM as the eluent.

Workup

  1. customat 150° C.
  2. customfor 2.5 h

Sources & evidence

ORD record
ord-d02682ed30fd476699b2ef2996eb93af
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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