Methyl Isocyanate → N-(3,4-dihydro-2,2-dioxo-3-methyl-1,2-benzoxathiin-8-ylsulfonyl)-N'-methylurea

HRID 845674Notes

Reaction equation

HRID 845674 reaction equation
[CH3:1][CH:2]1[CH2:7][C:6]2[CH:8]=[CH:9][CH:10]=[C:11]([S:12]([NH2:15])(=[O:14])=[O:13])[C:5]=2[O:4][S:3]1(=[O:17])=[O:16].[CH3:18][N:19]=[C:20]=[O:21].N12CCCN=C1CCCCC2>C(#N)C.O>[CH3:1][CH:2]1[CH2:7][C:6]2[CH:8]=[CH:9][CH:10]=[C:11]([S:12]([NH:15][C:20]([NH:19][CH3:18])=[O:21])(=[O:14])=[O:13])[C:5]=2[O:4][S:3]1(=[O:17])=[O:16]

Participants

6

Reactant 3

HCID 12228Methyl IsocyanateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 135920753,4-Dihydro-2,2-dioxo-3-methyl-1,2-benzoxathiin-8-ylsulfonamide

Product 1

HCID 19839353N-(3,4-dihydro-2,2-dioxo-3-methyl-1,2-benzoxathiin-8-ylsulfonyl)-N'-methylurea

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×

Procedure

A solution of 24.96 g of 3,4-dihydro-3-methyl-2,2-dioxo-1,2-benzoxathiin-8-ylsulfonamide in 120 ml of absolute acetonitrile is cooled to +8° C. After the addition of 6 ml of methyl isocyanate, a solution of 13.4 ml of 1,8-diazabicyclo[5.4.0]undec-7-ene in 15 ml of acetonitrile is added dropwise over 15 minutes at 10° C. The reaction mixture is stirred for a further hour at room temperature. The mixture is subsequently diluted with 180 ml of water. The product is precipitated by the dropwise addition of 48 ml of 2N hydrochloric acid. The precipitate is isolated and dried, affording 26.4 g of N-(3,4-dihydro-3-methyl-2,2-dioxo-1,2-benzoxathiin-8-ylsulfonyl)-N'-methylurea with a melting point of 235°-238° C.

Workup

  1. customThe product is precipitated by the dropwise addition of 48 ml of 2N hydrochloric acid
  2. customThe precipitate is isolated
  3. customdried

Sources & evidence

ORD record
ord-76bdd5250f1844c09bfe7ceefdae257e
Source dataset
uspto-grants-1988_07
Patent number
US04759791

Reaction notes

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