HCID 1712173, compound → HCID 12680596, compound

HRID 1775816Notes

Reaction equation

HRID 1775816 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([NH2:15])=O)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].O(C1C=CC(P2(=S)SP(=S)(C3C=CC(OC4C=CC=CC=4)=CC=3)[S:32]2)=CC=1)C1C=CC=CC=1>COCCOC.C1COCC1>[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13](=[S:32])[NH2:15])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 2

HCID 1712173HCID 1712173, compoundHCID 118134142,4-Bis(4-phenoxyphenyl)-2,4-dithioxo-1,3,2,4-dithiadiphosphetane

Product 1

HCID 12680596HCID 12680596, compoundYield 105.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To stirring suspension of 4-(heptyloxy)benzamide (1.24 g, 5.29 mmol) in DME (20 mL) and THF (10 mL) was added 2,4-bis(4-phenoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide (2.80 g, 5.29 mmol). The reaction mixture was stirred at room temperature for 16 h. The reaction mixture was concentrated onto silica and purified by column chromatography (0-60% EA in iso-hexanes) to afford 1.4 g (62%) of 4-(heptyloxy)benzothioamide as a yellow waxy solid. LCMS-ESI (m/z) calculated for C14H21NOS, 251.4. found 252.0 [M+H]+, tR=3.13 min. (Method 6).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 16 h
  2. concentrationThe reaction mixture was concentrated onto silica
  3. custompurified by column chromatography (0-60% EA in iso-hexanes)

Sources & evidence

ORD record
ord-c23694d1d82444ce80b4d74119e89b32
Source dataset
uspto-grants-2016_02
Patent number
US09260427B2

Reaction notes

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