Dichloromethane → HCID 70294436, compound

HRID 1421211Notes

Reaction equation

HRID 1421211 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:23]=[CH:24][C:25]=1[O:26][CH3:27])[CH:6]=[CH:7][C:8]1[C:14]2[CH:15]=[C:16]3[O:21][CH2:20][O:19][C:17]3=[CH:18][C:13]=2[CH2:12][C:11]([CH3:22])=[N:10][N:9]=1.ClCCl.[B-][N+](C)(C)C.C(=O)([O-])[O-].[Na+].[Na+]>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:23]=[CH:24][C:25]=1[O:26][CH3:27])[CH:6]=[CH:7][C:8]1[C:14]2[CH:15]=[C:16]3[O:21][CH2:20][O:19][C:17]3=[CH:18][C:13]=2[CH2:12][CH:11]([CH3:22])[NH:10][N:9]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 6327651Borane,N-dimethylmethanamine (1:1)HCID 53665039HCID 53665039, compound

Product 1

HCID 70294436HCID 70294436, compoundYield 85.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
25 °C

Procedure

To a solution of 2.04 g (5.6 mmoles) 1-(3,4-dimethoxystyryl)-4-methyl-7,8-methylenedioxy-5H-2,3-benzodiazepine in 40 ml of anhydrous dichloromethane 1.0 ml (8.4 mmoles) of borotrifluoride etherate is added under cooling with tap water, and 0.45 g (6.16 mmoles) of borane trimethylamine complex is added to it. The reaction mixture is stirred at 25° C. for 0.5 hour, and then 30 ml of 10% aqueous sodium carbonate solution are dropped to it under cooling with tap water, and the mixture is stirred further for 1 hour. The organic phase is separated, washed four times with 30 ml each of distilled water, dried and evaporated. The crystalline residue is suspended in 10 ml of ethanol, filtered, washed three times with 1 ml each of ethanol and dried at a temperature between 80° C. and 100° C. Thus 1.76 g of the desired product is obtained. M.p.: 166-168° C.

Workup

  1. additionis added to it
  2. stirringthe mixture is stirred further for 1 hour
  3. customThe organic phase is separated
  4. washwashed four times with 30 ml each of distilled water
  5. customdried
  6. customevaporated
  7. filtrationfiltered
  8. washwashed three times with 1 ml each of ethanol
  9. customdried at a temperature between 80° C. and 100° C

Sources & evidence

ORD record
ord-3ff0578575284240b3401a3d79449d81
Source dataset
uspto-grants-2000_06
Patent number
US06075018

Reaction notes

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