Ammonia → 2-chloro-5-(N-cyclopropylsulfamoyl)benzamide

HRID 59302Notes

Reaction equation

HRID 59302 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([S:11](=[O:17])(=[O:16])[NH:12][CH:13]2[CH2:15][CH2:14]2)=[CH:7][C:3]=1[C:4](O)=[O:5].C(Cl)Cl.C(Cl)(=O)C(Cl)=O.[NH3:27]>CN(C=O)C.C1COCC1>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([S:11](=[O:17])(=[O:16])[NH:12][CH:13]2[CH2:15][CH2:14]2)=[CH:7][C:3]=1[C:4]([NH2:27])=[O:5]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 16768315h-NTPDase8-IN-1

Product 1

HCID 900201032-chloro-5-(N-cyclopropylsulfamoyl)benzamideYield 91%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared by following procedure as described for step-2 of Intermediate-26 by using 2-chloro-5-(N-cyclopropylsulfamoyl)benzoic acid (3.0 g, 10.0 mmol), DCM (30 mL), oxalyl chloride, ammonia gas (1.2 mL, 13.0 mmol), DMF (2-3 drop) and THF (40 mL) to afford 2.500 g of the desired product. 1H NMR (300 MHz, DMSO d6): δ 0.41 (m, 2H), 0.47-0.51 (m, 2H), 2.12 (m, 2H), 7.74-7.82 (m, 4H), 8.11 (br s, 2H); MS (m/z): 273.00 (M−H)−.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-7eb60e671be54174b608f406f984b6c0
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Reaction notes

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