2-Amino-4,6-dimethyl pyrimidine → N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2,3-dihydro-2,2-dimethyl-7-benzofuransulfonamide

HRID 1981269Notes

Reaction equation

HRID 1981269 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[N:3]=1.[CH3:10][C:11]1([CH3:26])[CH2:15][C:14]2[CH:16]=[CH:17][CH:18]=[C:19]([S:20]([N:23]=[C:24]=[O:25])(=[O:22])=[O:21])[C:13]=2[O:12]1>O1CCCC1>[CH3:9][C:4]1[CH:5]=[C:6]([CH3:8])[N:7]=[C:2]([NH:1][C:24]([NH:23][S:20]([C:19]2[C:13]3[O:12][C:11]([CH3:26])([CH3:10])[CH2:15][C:14]=3[CH:16]=[CH:17][CH:18]=2)(=[O:21])=[O:22])=[O:25])[N:3]=1

Participants

4

Reactant 2

HCID 130212-Amino-4,6-dimethyl pyrimidineHCID 134241822,2-Dimethyl-2,3-dihydro-1-benzofuran-7-sulfonyl isocyanate

Product 1

HCID 13424183N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2,3-dihydro-2,2-dimethyl-7-benzofuransulfonamideYield 54.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.2 g of 2-amino-4,6-dimethylpyrimidine in 25 ml of tetrahydrofuran was added 2.5 g of 2,3-dihydro-2,2-dimethyl-7-benzofuransulfonyl isocyanate prepared above. After a slight exotherm the solution was stirred at room temperature for 4 hours. The solution was concentrated in vacuo to give a viscous oil that precipitated a solid from 10 ml of acetonitrile. The solid was recrystallized from acetonitrile to give 2 g of N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2,3-dihydro-2,2-dimethyl-7-benzofuransulfonamide, m.p. 203°-206° C. The IR spectrum showed a carbonyl absorption at 1680 cm-1 indicative of a sulfonylurea.

Workup

  1. customprepared above
  2. concentrationThe solution was concentrated in vacuo
  3. customto give a viscous oil
  4. customthat precipitated a solid from 10 ml of acetonitrile
  5. customThe solid was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-2c877a6f1c2846b8b78213b42efd28c5
Source dataset
uspto-grants-1985_04
Patent number
US04514211

Reaction notes

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