Thionyl Chloride → N-[1-(Chloromethyl)-2-methylpropyl]-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-carboxamide

HRID 48986Notes

Reaction equation

HRID 48986 reaction equation
[CH3:1][N:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5](=[O:12])[N:4]([C:13]2[CH:14]=[CH:15][C:16]3[S:20][N:19]=[C:18]([C:21]([NH:23][CH:24]([CH2:28]O)[CH:25]([CH3:27])[CH3:26])=[O:22])[C:17]=3[CH:30]=2)[C:3]1=[O:31].S(Cl)([Cl:34])=O>C(OCC)C>[Cl:34][CH2:28][CH:24]([NH:23][C:21]([C:18]1[C:17]2[CH:30]=[C:13]([N:4]3[C:5](=[O:12])[CH:6]=[C:7]([C:8]([F:11])([F:10])[F:9])[N:2]([CH3:1])[C:3]3=[O:31])[CH:14]=[CH:15][C:16]=2[S:20][N:19]=1)=[O:22])[CH:25]([CH3:27])[CH3:26]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 206342735-[3,6-Dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-N-[1-(hydroxymethyl)-2-methylpropyl]-1,2-benzisothiazole-3-carboxamide

Product 1

HCID 20634281N-[1-(Chloromethyl)-2-methylpropyl]-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-carboxamideYield 89.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-N-[1-(hydroxymethyl)-2-methylpropyl]-1,2-benzisothiazole-3-carboxamide(1.89 g, 4.14 mmol) at 0° C. is added thionyl chloride (5.00 ml). The resultant mixture is stirred one hour at 0° C. and two hours at room temperature. Anhydrous diethyl ether is added and the resultant suspension stirred vigorously for 1.75 hour. The suspension is filtered to afford the title compound as a cream-colored solid (1.77 g, 89.8%, mp>220° C.) which is identified by NMR spectral analysis.

Workup

  1. filtrationThe suspension is filtered

Sources & evidence

ORD record
ord-bab4403a44d440e5af4f1c168091dd17
Source dataset
uspto-grants-2004_03
Patent number
US06706663B2

Reaction notes

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