Phosphorus pentachloride → HCID 68183263, compound

HRID 513641Notes

Reaction equation

HRID 513641 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([NH2:12])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[CH3:13][C:14]1[C:19](C)=[CH:18][CH:17]=[CH:16][C:15]=1[NH:21][S:22](=[O:25])(=O)[O-:23].[Na+].P(Cl)(Cl)(Cl)(Cl)[Cl:28]>C1(C)C=CC=CC=1>[Cl:28][C:19]1[C:14]([CH3:13])=[C:15]([NH:21][S:22]([NH:12][C:9]2[CH:10]=[CH:11][C:2]([Cl:1])=[C:3]3[C:8]=2[N:7]=[CH:6][CH:5]=[CH:4]3)(=[O:25])=[O:23])[CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 24819Phosphorus pentachlorideHCID 2248605-Chloroquinolin-8-amine2×HCID 86669764HCID 86669764, compound2×

Product 1

HCID 68183263HCID 68183263, compoundYield 7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In the similar fashion using route 19 general procedure 42, 5-chloroquinolin-8-amine (Intermediate 27) (155 mg, 1.15 mmol), sodium (2,3-dimethylphenyl)sulfamate (Intermediate 21) (300 mg, 1.23 mmol), PCl5 (771 mg, 3.70 mmol), TEA (1.67 ml, 12.3 mmol) and toluene (10 ml) gave the title compound (24 mg, 7%) after purification by column chromatography with n-hexane/EtOAc (1:0-17:3) as the eluent followed by trituration from n-pentane.

Sources & evidence

ORD record
ord-a307f44ddb414526b8f92a2443060f2e
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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