4-Toluenesulfonyl chloride → HCID 135735617, compound

HRID 65684Notes

Reaction equation

HRID 65684 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:16]=[C:15]2[N:6]([C:7](=[O:17])[NH:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=32)[N:5]=1.[S:18](Cl)([C:21]1[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=1)(=[O:20])=[O:19]>N1C=CC=CC=1>[CH3:25][C:24]1[CH:26]=[CH:27][C:21]([S:18]([O:1][CH2:2][CH2:3][C:4]2[CH:16]=[C:15]3[N:6]([C:7](=[O:17])[NH:8][C:9]4[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=43)[N:5]=2)(=[O:20])=[O:19])=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 135735616HCID 135735616, compound

Product 1

HCID 135735617HCID 135735617, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

12.0 g (0.052 mole) of 2-(2-hydroxyethyl)-pyrazolo-[1,5-c]quinazolin-5(6H)-one is taken up in pyridine (120 ml), cooled down to 0° and treated with 11.0 g (0.058 mole or 1.1 equivalent) of 98% tosyl chloride. The mixture is stirred for 4 hours, keeping the temperature below 20° during the reaction period, after which it is poured onto 1.8 l. of ice-water and stirred until solids form. The off-white precipitates are filtered off and dried in vacuo at 100° for 3 hours. Yield: 17.43 g, m.p. 194°-196°; 87.4% crude yield.

Workup

  1. temperaturecooled down to 0°
  2. customthe temperature below 20°
  3. customduring the reaction period
  4. additionafter which it is poured onto 1.8 l
  5. customform
  6. customThe off-white precipitates
  7. filtrationare filtered off
  8. customdried in vacuo at 100° for 3 hours

Sources & evidence

ORD record
ord-9fbff57a096d4ba49d6c3cefaee6a92d
Source dataset
uspto-grants-1978_12
Patent number
US04128644

Reaction notes

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