Benzofuran → HCID 20496353, compound

HRID 1074377Notes

Reaction equation

HRID 1074377 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[N:3]=1.Cl[S:11]([N:14]=[C:15]=[O:16])(=[O:13])=[O:12].[O:17]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[CH:19]=[CH:18]1.[Cl-].[Al+3].[Cl-].[Cl-]>[N+](C)([O-])=O.O>[CH3:9][C:4]1[CH:5]=[C:6]([CH3:8])[N:7]=[C:2]([NH:1][C:15]([NH:14][S:11]([C:18]2[O:17][C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[CH:19]=2)(=[O:13])=[O:12])=[O:16])[N:3]=1

Participants

7

Reactant 4

HCID 9223BenzofuranHCID 130212-Amino-4,6-dimethyl pyrimidineHCID 70918Chlorosulfonyl isocyanateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 20496353HCID 20496353, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6375NitromethaneSolvent2×

Conditions

Temperature
-10 °C

Procedure

A suspension of 2.59 g of 2-amino-4,6-dimethylpyrimidine in 50 ml of nitromethane was cooled to -10° C. and treated with 2.0 ml of chlorosulfonyl isocyanate. After stirring for 0.5 hour at -10° C. a solution of 2.0 ml of benzofuran in 10 ml of nitromethane was added dropwise followed by 2.8 g of aluminum chloride. The mixture was stirred and heated at reflux until TLC monitoring indicated the disappearance of starting material. The mixture was cooled, poured into water, extracted with methylene chloride, the extract washed with water, dried over magnesium sulfate, filtered and concentrated in vacuo to a dark oil. Trituration with dichloromethane followed by washing with acetonitrile gave the desired product as a mixture of 2- and 3-positional isomers, m.p. 206°-218° C. dec. The product exhibited IR bands at 3300 (NH), 1710 (C=O, 1340 (SO2) and 1140 (SO2) cm-1 and NMR absorptions at δ 2.4 (s, pyrimidine methyls) and 6.3-8.0 (m, aromatic and pyrimidine H's).

Workup

  1. additionwas added dropwise
  2. temperatureheated
  3. temperatureat reflux until TLC monitoring
  4. temperatureThe mixture was cooled
  5. extractionextracted with methylene chloride
  6. washthe extract washed with water
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo to a dark oil
  10. washby washing with acetonitrile

Sources & evidence

ORD record
ord-4f50dc3e8b2a4ce6a4f867ff18ad1463
Source dataset
uspto-grants-1983_07
Patent number
US04391627

Reaction notes

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