Hydrochloric Acid → HCID 837239, compound

HRID 1414262Notes

Reaction equation

HRID 1414262 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[CH:20]=[CH:19][C:10]([C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:12])=[CH:9][CH:8]=1.N1C=CC=CC=1.Cl>O>[C:11]([C:10]1[CH:9]=[CH:8][C:7]([NH:6][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:20][CH:19]=1)(=[O:12])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 143464-AminobenzophenoneHCID 31297Methanesulfonyl chloride

Product 1

HCID 837239HCID 837239, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

Methanesulfonyl chloride (35.0 g., 0.305 mole) is added dropwise over a 20 min. period with stirring to a solution of 4-aminobenzophenone (60.2 g., 0.305 mole) in 475 ml. of pyridine cooled at 0°-10°C. After the addition is completed, stirring at 0°-10°C. is continued for 4 hrs., and then for an additional 12 hrs. at room temperature. The solution is then heated to 90°C. for 1 hr., allowed to cool, poured into 1.0.1. of water, and then acidified with concentrated hydrochloric acid to pH 1.0. The precipitate which forms is collected on a filter, washed with water, and recrystallized from isopropanol without previous drying to give 70.0 g. (83% yield), m.p. 145-147°C.

Workup

  1. additionAfter the addition
  2. wait, and then for an additional 12 hrs
  3. customat room temperature
  4. temperatureto cool
  5. additionpoured into 1.0.1
  6. customThe precipitate which forms is collected on a filter
  7. washwashed with water
  8. customrecrystallized from isopropanol
  9. customwithout previous drying
  10. customto give 70.0 g

Sources & evidence

ORD record
ord-c567f7eaf48141ccb2bb19e75a3190cf
Source dataset
uspto-grants-1977_01
Patent number
US04001229

Reaction notes

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