Ethyl Acetate → phenyl N-[[methyl[[[2,3-dihydro-2,2-dimethyl-7-benzofuranyl]oxy]carbonyl]amino]thio]-2-methyl-propiothioimidate

HRID 2418699

Reaction equation

HRID 2418699 reaction equation
[CH3:1][N:2]([C:16](F)=[O:17])[S:3][N:4]=[C:5]([S:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH:6]([CH3:8])[CH3:7].[CH3:19][C:20]1([CH3:30])[CH2:24][C:23]2[CH:25]=[CH:26][CH:27]=[C:28]([OH:29])[C:22]=2[O:21]1.C(OC(=O)C)C>[Cl-].C([N+](CC1C=CC=CC=1)(C)C)CCCCCCCCCCCCCCC.C(Cl)Cl.[OH-].[Na+].CCCCCC>[CH3:1][N:2]([C:16]([O:29][C:28]1[C:22]2[O:21][C:20]([CH3:30])([CH3:19])[CH2:24][C:23]=2[CH:25]=[CH:26][CH:27]=1)=[O:17])[S:3][N:4]=[C:5]([S:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[CH:6]([CH3:8])[CH3:7]

Participants

8

Reactant 3

HCID 8857Ethyl AcetateHCID 152782,3-Dihydro-2,2-dimethyl-7-benzofuranolHCID 54390931phenyl N-[[methyl[fluorocarbonyl]amino]thio]-2-methylpropiothioimidate

Product 1

HCID 53887993phenyl N-[[methyl[[[2,3-dihydro-2,2-dimethyl-7-benzofuranyl]oxy]carbonyl]amino]thio]-2-methyl-propiothioimidate

Reagents, catalysts & solvents 4

HCID 31202Benzylhexadecyldimethylammonium chlorideCatalystHCID 6344DichloromethaneSolventHCID 8058HexaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of phenyl N-[[methyl[fluorocarbonyl]amino]thio]-2-methylpropiothioimidate (7.8 g, 27 mmoles) as prepared in Preparation 1 and cetylbenzyldimethylammonium chloride (0.9 g) in methylene chloride (150 ml) is added a solution of 2,3-dihydro-2,2-dimethyl-7-benzofuranol (4.5 g, 27 mmoles) in 0.18N sodium hydroxide (150 ml). The two-phase reaction mixture is stirred vigorously at ambient temperature for 90 minutes. The layers are separated and the organic phase dried over anhydrous sodium sulfate. Removal of the solvent gives a clear brown oil. This material is transferred to a column of silica gel and the chromatogram developed with a solvent mixture consisting of 8% ethylacetate in Skellysolve B. From the appropriate fraction there is obtained a white solid which is recrystallized from hexane to give the product phenyl N-[[methyl[[[2,3-dihydro-2,2-dimethyl-7-benzofuranyl]oxy]carbonyl]amino]thio]-2-methyl-propiothioimidate as a white crystalline solid, mp 104°-106°.

Workup

  1. customThe two-phase reaction mixture
  2. customThe layers are separated
  3. dry with materialthe organic phase dried over anhydrous sodium sulfate
  4. customRemoval of the solvent
  5. customgives a clear brown oil
  6. customFrom the appropriate fraction there is obtained a white solid which
  7. customis recrystallized from hexane

Sources & evidence

ORD record
ord-ca992ac6f3b3446ea815bab7424422d2
Source dataset
uspto-grants-1984_09
Patent number
US04473580

Linked notes

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