Dichloromethane → HCID 178483738, compound

HRID 2399240Notes

Reaction equation

HRID 2399240 reaction equation
[CH3:1][N:2]([CH3:44])[CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][C:12]([NH:38][CH2:39][CH2:40][N:41]([CH3:43])[CH3:42])=[C:13]3[C:14](=[O:37])[C:15]4[C:20]([C:7]([C:8]=23)=[N:6]1)=[C:19]([O:21]CC1C=CC=CC=1)[CH:18]=[CH:17][C:16]=4[O:29]CC1C=CC=CC=1.ClCCl.B(Cl)(Cl)Cl>CO>[OH:29][C:16]1[CH:17]=[CH:18][C:19]([OH:21])=[C:20]2[C:15]=1[C:14](=[O:37])[C:13]1[C:8]3[C:7]2=[N:6][N:5]([CH2:4][CH2:3][N:2]([CH3:44])[CH3:1])[C:9]=3[CH:10]=[CH:11][C:12]=1[NH:38][CH2:39][CH2:40][N:41]([CH3:43])[CH3:42]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 25135Boron TrichlorideHCID 19387334HCID 19387334, compound

Product 1

HCID 178483738HCID 178483738, compoundYield 47.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.35 g (0.59 mmol) of 2-[2-(dimethylamino)-ethyl]-5-[[2-(dimethylamino)ethyl]amino]-7,10-bis(phenylmethoxy)-anthra[1,9-cd]pyrazol-6(2H)-one is dissolved in cold, dry dichloromethane (4 ml) and boron trichloride (4 ml, 1M solution in dichloromethane) is added dropwise over 30 minutes under argon. The reaction mixture is maintained at 0°-5° C. for 1 hour and then treated dropwise with cold methanol under argon. The mixture is then maintained at room temperature for 2 hours and then evaporated to dryness in vacuo. The resulting crude hydrochloride salt is dissolved in a minimum volume of methanol and then chromatographed on a column of silica gel (60A) using an eluting solvent of dichloromethane:methanol (80:20 v/v) and then dichloromethane:methanol:triethylamine (80:20:1 v/v). The major red band is collected and evaporated in vacuo to yield 0.115 g of the title compound as a red solid, m.p. 101 C; λmax (methanol) (E/cm/M) 580 nm (11200), 334 nm (7463), 290 nm (5667).

Workup

  1. additionis added dropwise over 30 minutes under argon
  2. temperatureThe reaction mixture is maintained at 0°-5° C. for 1 hour
  3. customevaporated to dryness in vacuo
  4. dissolutionThe resulting crude hydrochloride salt is dissolved in a minimum volume of methanol
  5. customchromatographed on a column of silica gel (60A)
  6. customThe major red band is collected
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-04f187f97f2a48d08c3b8b48dbf1a087
Source dataset
uspto-grants-1995_09
Patent number
US05447950

Reaction notes

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