Pyridine → HCID 68183282, compound

HRID 513532Notes

Reaction equation

HRID 513532 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10](Cl)(=[O:12])=[O:11])([O-:3])=[O:2].[S:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[C:22]([NH2:23])[C:17]=2[N:16]=[CH:15]1.[N+](C1C2N=CSC=2C=CC=1)([O-])=O.N1C=CC=CC=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[S:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[C:22]([NH:23][S:10]([C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N+:1]([O-:3])=[O:2])(=[O:12])=[O:11])[C:17]=2[N:16]=[CH:15]1

Participants

7

Reactant 4

HCID 1049PyridineHCID 155402-Nitrobenzenesulfonyl chlorideHCID 2984904-BenzothiazolamineHCID 601876benzothiazole, 4-nitro-

Product 1

HCID 68183282HCID 68183282, compoundYield 45.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

In a similar fashion using route 14 general procedure 27, 2-nitrobenzenesulfonyl chloride (1.7 g, 7.9 mmol), benzothiazol-4-ylamine (Intermediate 222) (1.0 g, 6.6 mmol), DMAP (cat), pyridine (2 ml, 24.8 mmol) and DCM (10 ml) at 0° C. for 5 h, gave the title compound (1.0 g, 45%) which was used in the next step without further purification.

Workup

  1. customat 0° C.
  2. customfor 5 h

Sources & evidence

ORD record
ord-f67e8c71edf14e8b9a0798307751c8ce
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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