Diisopropyl Ether → 4-[[O-[N-Methyl-N-(4-chlorophenylthiosulfenyl)carbamoyl]oximino]]-5-methyl-1,3-oxathiolane

HRID 224378Notes

Reaction equation

HRID 224378 reaction equation
[CH3:1][CH:2]1[O:6][CH2:5][S:4][C:3]1=[N:7][OH:8].[CH3:9][N:10]([S:14][S:15][C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=1)[C:11](F)=[O:12].C(N(CC)CC)C.C(OC(C)C)(C)C>O1CCOCC1.C(OCC)(=O)C>[CH3:9][N:10]([S:14][S:15][C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=1)[C:11]([O:8][N:7]=[C:3]1[CH:2]([CH3:1])[O:6][CH2:5][S:4]1)=[O:12]

Participants

7

Reactant 4

HCID 7914Diisopropyl EtherHCID 8471TriethylamineHCID 23333002N-methyl-N-(4-chlorophenylthiosulfenyl)carbamoyl fluorideHCID 71364792N-(5-Methyl-1,3-oxathiolan-4-ylidene)hydroxylamine

Product 1

HCID 537557594-[[O-[N-Methyl-N-(4-chlorophenylthiosulfenyl)carbamoyl]oximino]]-5-methyl-1,3-oxathiolane

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

4-[[O-[N-Methyl-N-(4-chlorophenylthiosulfenyl)carbamoyl]oximino]]-5-methyl-1,3-oxathiolane was prepared according to the procedure described in Example I by reacting 4.0 g (0.03 m) of 5-methyl-4-oximino-1,3-oxathiolane, 7.55 g (0.03 m) of N-methyl-N-(4-chlorophenylthiosulfenyl)carbamoyl fluoride and 3.07 g (0.03 m) of triethylamine in 50 ml of dioxane. Addition of isopropyl ether and ethyl acetate to the residual oil and cooling yielded 2.37 g of a white solid, m.p. 71°-73° C.

Workup

  1. temperaturecooling

Sources & evidence

ORD record
ord-44878161322946f99f824831783d4e0b
Source dataset
uspto-grants-1980_11
Patent number
US04232035

Reaction notes

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