Ammonia → HCID 11813010, compound

HRID 1593948Notes

Reaction equation

HRID 1593948 reaction equation
[N:1]1([CH2:6][CH2:7][C:8]([NH:10][C:11]2[CH:24]=[CH:23][C:22]3[NH:21][C:20]4[C:15](=[CH:16][CH:17]=[C:18]([NH:25][C:26](=[O:34])[CH2:27][CH2:28][N:29]5[CH2:33][CH2:32][CH2:31][CH2:30]5)[CH:19]=4)[C:14](=O)[C:13]=3[CH:12]=2)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.P(Cl)(Cl)(Cl)(Cl)[Cl:37].P(Cl)(Cl)(Cl)=O.N>C(Cl)(Cl)Cl>[Cl:37][C:14]1[C:15]2[C:20]([N:21]=[C:22]3[C:13]=1[CH:12]=[C:11]([NH:10][C:8](=[O:9])[CH2:7][CH2:6][N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)[CH:24]=[CH:23]3)=[CH:19][C:18]([NH:25][C:26](=[O:34])[CH2:27][CH2:28][N:29]1[CH2:33][CH2:32][CH2:31][CH2:30]1)=[CH:17][CH:16]=2

Participants

6

Reactant 4

HCID 222AmmoniaHCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 10116404HCID 10116404, compound

Product 1

HCID 11813010HCID 11813010, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A suspension of 2,6-bis(3-pyrrolidinopropionamido)acridone AR-ACO-10 (2.0 g, 4.2 mmol) in CHCl3 (40 mL) was treated with phosphorus pentachloride (0.9 g, 4.2 mmol), followed by cautious addition of phosphorus oxychloride (50 mL). This suspension was stirred at room temp. for 30 min and brought to a gentle reflux over 1 hr. Gentle reflux was maintained for 26 hr. The reaction mixture was cooled to rt then slowly dropped onto ice (˜600 mL) over 10 min. The aqueous mixture was made basic to pH 7/8 with ammonia whilst maintaining a temp. <25° C. The aqueous layer was extracted with CHCl3 (5×200 mL). The organic extracts were combined, washed with brine (200 mL), dried (Na2SO4) and concentrated. The resulting solid was tritrated with diethyl ether (30 mL) to give the desired product (1.3 g, 62%) as a light brown solid.

Workup

  1. temperaturea gentle reflux over 1 hr
  2. temperatureGentle reflux
  3. temperaturewas maintained for 26 hr
  4. additionthen slowly dropped onto ice (˜600 mL) over 10 min
  5. temperaturewhilst maintaining a temp
  6. custom<25° C
  7. extractionThe aqueous layer was extracted with CHCl3 (5×200 mL)
  8. washwashed with brine (200 mL)
  9. dry with materialdried (Na2SO4)
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-6ea9b47554a8471ea97c7ea480f7563c
Source dataset
uspto-grants-2007_11
Patent number
US07300930B2

Reaction notes

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