Diethyl Ether → 4-Isocyanato-5,6-dihydro-1-benzothiophen-7(4H)-one

HRID 1730987Notes

Reaction equation

HRID 1730987 reaction equation
[O:1]=[C:2]1[C:7]2[S:8][CH:9]=[CH:10][C:6]=2[CH:5]([N+:11]#[C-:12])[CH2:4][CH2:3]1.C1(C)C=CC(S(O)(=O)=[O:20])=CC=1.CCOCC>CS(C)=O>[O:1]=[C:2]1[C:7]2[S:8][CH:9]=[CH:10][C:6]=2[CH:5]([N:11]=[C:12]=[O:20])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6101p-Toluenesulfonic acidHCID 214946344-Isocyano-5,6-dihydro-1-benzothiophen-7(4H)-one

Product 1

HCID 203489024-Isocyanato-5,6-dihydro-1-benzothiophen-7(4H)-one

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 4,5,6,7-tetrahydro-7-oxobenzo[b]thien-4-ylisocyanide (9.5 g) in dry dimethylsulfoxide (4.63 g) is stirred under a nitrogen atmosphere while anhydrous p-toluenesulfonic acid (0.93 g) is added in small portions over an hour. The mixture is heated below 50° C. After 1.25 hours the reaction mixture is cooled and ether (3 × 3 ml) added, and the ether solution is then decanted. The ether solution contains the title isocyanate, and is used as is.

Workup

  1. additionis added in small portions over an hour
  2. temperatureThe mixture is heated below 50° C
  3. temperatureAfter 1.25 hours the reaction mixture is cooled
  4. customthe ether solution is then decanted

Sources & evidence

ORD record
ord-8eb3b5c5185846c389a80c567542aba5
Source dataset
uspto-grants-1976_11
Patent number
US03994924

Reaction notes

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