Oxalyl chloride → 2-Furansulfonyl isocyanate

HRID 27346

Reaction equation

HRID 27346 reaction equation
C(Cl)(=O)[C:2](Cl)=[O:3].N12CCC(CC1)CN2.[O:15]1[CH:19]=[CH:18][CH:17]=[C:16]1[S:20]([NH2:23])(=[O:22])=[O:21]>C1(C)C=CC=CC=1>[O:15]1[CH:19]=[CH:18][CH:17]=[C:16]1[S:20]([N:23]=[C:2]=[O:3])(=[O:22])=[O:21]

Participants

5

Reactant 3

HCID 65578Oxalyl chlorideHCID 136165Diazabicyclo(2.2.2)octaneHCID 13668256Furan-2-sulfonamide

Product 1

HCID 233424782-Furansulfonyl isocyanate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Dry toluene (150 ml), 25 ml of oxalyl chloride (295), and a trace of DABCO (diaza-bicyclo[2.2.2]octane) were heated to 90°. Ten g of 2-furansulfonamide was added over a 15 minute period and the mixture was held at 95° for 2 hours. After filtering, the solvent was removed under vacuum to yield 2.1 g of an oil showing the characteristic isocyanate absorption in the infrared (2280 cm-1).

Workup

  1. filtrationAfter filtering
  2. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-989e8416a8634b9e8cbdc96eb0350707
Source dataset
uspto-grants-1980_09
Patent number
US04221585

Linked notes

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