Phosgene → 2,2-Dimethyl-2,3-dihydro-1-benzofuran-7-sulfonyl isocyanate

HRID 280472Notes

Reaction equation

HRID 280472 reaction equation
C(N[C:6]([NH:8][S:9]([C:12]1[C:20]2[O:19][C:18]([CH3:22])([CH3:21])[CH2:17][C:16]=2[CH:15]=[CH:14][CH:13]=1)(=[O:11])=[O:10])=[O:7])CCC.C1N2CCN(CC2)C1.C(Cl)(Cl)=O>C1(C)C(C)=CC=CC=1>[CH3:21][C:18]1([CH3:22])[CH2:17][C:16]2[CH:15]=[CH:14][CH:13]=[C:12]([S:9]([N:8]=[C:6]=[O:7])(=[O:11])=[O:10])[C:20]=2[O:19]1

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 9237DabcoHCID 13424181N-(butylaminocarbonyl)-2,3-dihydro-2,2-dimethyl-7-benzofuransulfonamide

Product 1

HCID 134241822,2-Dimethyl-2,3-dihydro-1-benzofuran-7-sulfonyl isocyanate

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A suspension of 22 g of the N-(n-butylaminocarbonyl)-2,3-dihydro-2,2-dimethyl-7-benzofuransulfonamide prepared in Example 3, in 125 ml of xylene containing 0.3 g of DABCO was heated at 130°-135° C. while 5.3 ml of phosgene was added portionwise at a rate to maintain a reflux temperature of 130°-135° C. The mixture was refluxed for an additional 1.5 hours, cooled under nitrogen, and concentrated to dryness in vacuo. A sample of the crude oily product displayed a characteristic sulfonyl isocyanate band in the IR at 2200 cm-1.

Workup

  1. additionwas added portionwise at a rate
  2. temperatureto maintain a reflux temperature of 130°-135° C
  3. temperatureThe mixture was refluxed for an additional 1.5 hours
  4. temperaturecooled under nitrogen
  5. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-daa8ae17caf6483aacef8821411ca96a
Source dataset
uspto-grants-1986_05
Patent number
US04589909

Reaction notes

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