Butyl isocyanate → N-(butylaminocarbonyl)-2,3-dihydro-2,2-dimethyl-7-benzofuransulfonamide
Reaction equation
[CH3:1][C:2]1([CH3:15])[CH2:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([S:11]([NH2:14])(=[O:13])=[O:12])[C:4]=2[O:3]1.[CH2:16]([N:20]=[C:21]=[O:22])[CH2:17][CH2:18][CH3:19].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH2:16]([NH:20][C:21]([NH:14][S:11]([C:10]1[C:4]2[O:3][C:2]([CH3:15])([CH3:1])[CH2:6][C:5]=2[CH:7]=[CH:8][CH:9]=1)(=[O:13])=[O:12])=[O:22])[CH2:17][CH2:18][CH3:19]Participants
5
Procedure
A solution of 19 g of 2,3-dihydro-2,2-dimethyl-7-benzofuransulfonamide prepared in Example 2 and 9.9 g of n-butyl isocyanate in 200 ml of 2-butanone was refluxed with 11.5 g of anhydrous potassium carbonate for 7 hours. The resulting mixture was concentrated to dryness in vacuo. The residue was taken up in 400 ml of water and extracted once with 100 ml of ethyl ether. The aqueous layer was acidified with 2N HCl and the resulting mixture was filtered and suction dried. The still slightly wet solid was washed once with 100 ml of hot acetonitrile, then suction dried an additional 8 hours to give 23 g of N-(butylaminocarbonyl)-2,3-dihydro-2,2-dimethyl-7-benzofuransulfonamide, m.p. 200°-203° C.
Workup
- concentrationThe resulting mixture was concentrated to dryness in vacuo
- extractionextracted once with 100 ml of ethyl ether
- filtrationthe resulting mixture was filtered
- customsuction dried
- washThe still slightly wet solid was washed once with 100 ml of hot acetonitrile
- customsuction dried an additional 8 hours
Sources & evidence
- ORD record
- ord-c31eca0044504bbfb9761f9214d3ea51
- Source dataset
- uspto-grants-1986_05
- Patent number
- US04589909
Reaction notes
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