Water → HCID 86129805, compound

HRID 2240477Notes

Reaction equation

HRID 2240477 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([CH2:13][N+:14]#[C-:15])(=[O:12])=[O:11])=[CH:6][CH:5]=1.Br[CH:17]([CH:21]1[CH2:23][CH2:22]1)[CH2:18][CH2:19]Br.O>C(OCC)C.CS(C)=O>[CH:21]1([CH:17]2[CH2:18][CH2:19][C:13]2([N+:14]#[C-:15])[S:10]([C:7]2[CH:6]=[CH:5][C:4]([CH3:3])=[CH:9][CH:8]=2)(=[O:12])=[O:11])[CH2:23][CH2:22]1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 161915Tosylmethyl isocyanideHCID 13485105HCID 13485105, compound

Product 1

HCID 86129805HCID 86129805, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 3283Diethyl EtherSolvent2×

Procedure

In a sulfonation flask 11.1 g (0.28 mol) sodium hydride was suspended in a mixture of 80 ml diethylether and 220 ml DMSO. Then a solution of 19.9 g (0.1 mol) TosMIC and 28.2 g (0.115 mol) (1.3-dibromopropyl)cyclopropane in 30 ml diethylether and 80 ml DMSO was added in 90 minutes. After stirring for 1.5 hours, 70 ml of water was added slowly under ice cooling. The first crop of product was filtered off (16.3 g) and the mother liquor evaporated. The raw material obtained from the mother liquor was then purified by flash chromatography over silicagel (eluent: hexane/ethylacetate 2:1). Overall yield: 19.0 g (68% of theory) of 1-(2-cyclopropyl-1-isocyanocyclobutanesulfonyl)-4-methylbenzene in the form of a solid.

Workup

  1. filtrationThe first crop of product was filtered off (16.3 g)
  2. customthe mother liquor evaporated

Sources & evidence

ORD record
ord-2b56492468be4567bf1d6f97d943389a
Source dataset
uspto-grants-2010_05
Patent number
US07723371B2

Reaction notes

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