Dichloromethane → HCID 178448704, compound

HRID 1199746Notes

Reaction equation

HRID 1199746 reaction equation
[CH2:1]([N:5]1[C:12](=[O:13])[CH2:11][C:9](=[O:10])[N:8]([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[C:6]1=[O:7])[CH2:2][CH2:3][CH3:4].C1(C)C=CC(S([N:29]=[N+:30]=[N-])(=O)=O)=CC=1.C(N(CC)CC)C.ClCCl>C(#N)C>[CH2:1]([N:5]1[C:12](=[O:13])[C:11](=[N+:29]=[N-:30])[C:9](=[O:10])[N:8]([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[C:6]1=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 13661p-Toluenesulfonyl azideHCID 14848100HCID 14848100, compound

Product 1

HCID 178448704HCID 178448704, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
2 °C

Procedure

80 mL of reagent grade acetonitrile and 6.65 gm (0.025 mole) of 1-(1-butyl)-3-cyclohexylbarbituric acid were added to a dry 250 mL 3-neck round bottom flask equipped with a thermometer, pressure equalizing dropping funnel capped by a drying tube, nitrogen inlet and magnetic stirrer. The stirred solution was cooled to 2° C. in an ice bath. Then a solution of 5.75 gm (0.029 mole) of p-toluenesulfonyl azide in 20 mL of acetonitrile was added to the reaction flask. A solution of 3.20 gm (0.0317 mole) of triethylamine in 20 mL of reagent grade dichloromethane was placed in the dropping funnel and slowly added to the reaction flask, while keeping the temperature below 3° C. The flask temperature was kept below 3° C. for 1 hour. The stirred reaction flask was allowed to warm to room temperature (20° C.) and kept at room temperature for 12 hours.

Workup

  1. customequipped with a thermometer, pressure
  2. customcapped by a drying tube, nitrogen inlet and magnetic stirrer
  3. additionslowly added to the reaction flask
  4. customthe temperature below 3° C
  5. customThe stirred reaction flask
  6. temperatureto warm to room temperature (20° C.)
  7. waitkept at room temperature for 12 hours

Sources & evidence

ORD record
ord-a3aaf410ba904e71b671db5787ec800e
Source dataset
uspto-grants-1990_02
Patent number
US04902784

Reaction notes

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