Dichloromethane → N-[[(7-chloro-2,2,3,3-tetrafluorobenzothien-5-yl)amino]-carbonyl]-2-chlorobenzamide

HRID 980249

Reaction equation

HRID 980249 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].C(Cl)(=O)[C:12](Cl)=[O:13].[NH2:17][C:18]1[CH:19]=[C:20]([Cl:31])[C:21]2[S:25][C:24]([F:27])([F:26])[C:23]([F:29])([F:28])[C:22]=2[CH:30]=1.C(Cl)Cl>C1(C)C=CC=CC=1>[Cl:31][C:20]1[C:21]2[S:25][C:24]([F:26])([F:27])[C:23]([F:29])([F:28])[C:22]=2[CH:30]=[C:18]([NH:17][C:12]([NH:6][C:4](=[O:5])[C:3]2[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=2[Cl:1])=[O:13])[CH:19]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 691112-ChlorobenzamideHCID 202224185-Amino-7-chloro-2,2,3,3-tetrafluoro-2,3-dihydrobenzothiophene

Product 1

HCID 13785000N-[[(7-chloro-2,2,3,3-tetrafluorobenzothien-5-yl)amino]-carbonyl]-2-chlorobenzamideYield 51.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a manner similar to Step D of Example 1, the reaction of 0.58 g (0.0037 mole) 2-chlorobenzamide, 0.52 g (0.0051 mole) oxalyl chloride, 0.95 g (0.0037 mole) 5-amino-7-chloro-2,2,3,3-tetrafluoro-2,3-dihydrobenzothiophene, and 5 ml of methylene chloride in 75 ml of toluene produced 0.84 g of N-[[(7-chloro-2,2,3,3-tetrafluorobenzothien-5-yl)amino]-carbonyl]-2-chlorobenzamide as a solid (mp 140°-142° C.), compound 9 of Table 1.

Sources & evidence

ORD record
ord-478995f7001b4f6da4bccc09efe97d9c
Source dataset
uspto-grants-1987_01
Patent number
US04636523

Linked notes

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