3-Chloropropionyl chloride → HCID 21074075, compound

HRID 1373059Notes

Reaction equation

HRID 1373059 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][C:13]2[NH:12][C:11]3[C:6](=[CH:7][C:8]([NH2:16])=[CH:9][CH:10]=3)[C:5](=[O:17])[C:4]=2[CH:3]=1.[Cl:18][CH2:19][CH2:20][C:21](Cl)=[O:22]>>[Cl:18][CH2:19][CH2:20][C:21]([NH:16][C:8]1[CH:9]=[CH:10][C:11]2[NH:12][C:13]3[C:4](=[CH:3][C:2]([NH:1][C:21](=[O:22])[CH2:20][CH2:19][Cl:18])=[CH:15][CH:14]=3)[C:5](=[O:17])[C:6]=2[CH:7]=1)=[O:22]

Participants

3

Reactant 2

HCID 693643-Chloropropionyl chlorideHCID 210740792,7-Diaminoacridin-9(10H)-one

Product 1

HCID 21074075HCID 21074075, compoundYield 81%

Procedure

A suspension of 2,7-diamino-9(10H)-acridone 12 (13.44 g, 60 mmol), in 3-chloropropionyl chloride (3-CPC) (240 mL) was stirred at 90° C. for 4 hr and then heated under reflux for 2 hr. The resultant mixture was cooled to 0° C. after which the product was collected on a glass sinter. The product was washed with acetone (60 mL) followed by toluene (2×60 mL), more acetone (4×60 mL), dry ether (2×60 mL) and finally hexane (2×60 mL). The product was dried over P2O5 under vacuum to yield an olive-green solid (19.68 g, 81%).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2 hr
  3. customwas collected on a glass sinter
  4. washThe product was washed with acetone (60 mL)
  5. dry with materialThe product was dried over P2O5 under vacuum

Sources & evidence

ORD record
ord-742a9fbd175a4eb6a750f97d57405e40
Source dataset
uspto-grants-2007_01
Patent number
US07160896B2

Reaction notes

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