Sulfuryl chloride → 2-Chloromethyl-4-isopropyl-5,6-dimethoxysaccharin

HRID 266470Notes

Reaction equation

HRID 266470 reaction equation
N[S:2]([C:5]1[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[C:12]([CH:20]([CH3:22])[CH3:21])[C:6]=1[C:7]([N:9](C)[CH3:10])=[O:8])(=[O:4])=[O:3].C(C1C(OC)=C(OC)C=C2C=1C(=O)NS2(=O)=O)(C)C.C1(SC[Cl:50])C=CC=CC=1.C1(SCN2C(=O)C3C(=CC(OC)=C(OC)C=3C(C)C)S2(=O)=O)C=CC=CC=1.S(Cl)(Cl)(=O)=O>C(OCC)(=O)C.CCCCCC>[Cl:50][CH2:10][N:9]1[C:7](=[O:8])[C:6]2[C:5](=[CH:15][C:14]([O:16][CH3:17])=[C:13]([O:18][CH3:19])[C:12]=2[CH:20]([CH3:22])[CH3:21])[S:2]1(=[O:4])=[O:3]

Participants

7

Reactant 5

HCID 24648Sulfuryl chlorideHCID 81623Chloromethyl phenyl sulphideHCID 152910774-Isopropyl-5,6-dimethoxysaccharinHCID 54046916HCID 54046916, compoundHCID 70052898HCID 70052898, compound

Product 1

HCID 700449542-Chloromethyl-4-isopropyl-5,6-dimethoxysaccharinYield 85%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

By the method of Example 22A 2-aminosulfonyl-4,5-dimethoxy-6-isopropyl-N,N-dimethylbenzamide (10.75 g) was prepared and cyclized to 4-isopropyl-5,6-dimethoxysaccharin (mp 186°-188° C. from ether-hexane), phenylthiomethylation of part (5 g) of which with chloromethyl phenyl sulfide (2.48 mL) gave 2-phenylthiomethyl-4-isopropyl-5,6-dimethoxysaccharin (4.07 g), reaction of which with sulfuryl chloride (three molar equivalents) gave 2-chloromethyl-4-isopropyl-5,6-dimethoxysaccharin, 85% yield, mp 117°-119° C. from ethyl acetate-hexane.

Workup

  1. customgave

Sources & evidence

ORD record
ord-6044b58b956f4f54b6d25cf4b9ff0156
Source dataset
uspto-grants-1997_07
Patent number
US05650422

Reaction notes

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