3-Chloropropionyl chloride → HCID 58780842, compound

HRID 1593945Notes

Reaction equation

HRID 1593945 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[C:9]([NH2:16])[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:1][C:2]1[CH:15]=[CH:14][C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[C:9]([NH:16][C:21](=[O:22])[CH2:20][CH2:19][Cl:18])[CH:10]=3)[C:5](=[O:17])[C:4]=2[CH:3]=1)=[O:22]

Participants

3

Reactant 2

HCID 693643-Chloropropionyl chlorideHCID 21074071HCID 21074071, compound

Product 1

HCID 58780842HCID 58780842, compound

Conditions

Temperature
90 °C

Procedure

2,6-Diamino-9(10H)-acridone (AR-ACO-8, 8.40 g, 37.3 mmol was suspended in 3-chloropropionyl chloride (100 mL), stirred at room temperature for 1 hr, at 90° C. for 1 hr, and at reflux for 6 hr. Allowed to stand at room temperature overnight and then chilled with ice-water. The product was collected and washed with acetone (2×30 mL) followed by toluene (3×30 mL), acetone again (4×30 mL), ethanol (2×30 mL), dry ether (2×30 mL) and finally hexane (2×30 mL). The product was dried over P2O5 under vacuum to yield a yellow solid AR-ACO-09 (12.96 g, 86%).

Workup

  1. temperatureat reflux for 6 hr
  2. waitAllowed to stand at room temperature overnight
  3. customThe product was collected
  4. washwashed with acetone (2×30 mL)
  5. dry with materialThe product was dried over P2O5 under vacuum
  6. customto yield a yellow solid AR-ACO-09 (12.96 g, 86%)

Sources & evidence

ORD record
ord-f666f598a1b44641b1402ab7ff138988
Source dataset
uspto-grants-2007_11
Patent number
US07300930B2

Reaction notes

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