Dimethylamine → HCID 54567917, compound

HRID 1702447Notes

Reaction equation

HRID 1702447 reaction equation
Cl[CH2:2][C:3]([N:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[NH:9][C:8](=[O:16])[C:7]2=[CH:17][S:18][CH:19]=[C:6]12)=[O:4].[CH3:20][NH:21][CH3:22].C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[CH3:20][N:21]([CH2:2][C:3]([N:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[NH:9][C:8](=[O:16])[C:7]2=[CH:17][S:18][CH:19]=[C:6]12)=[O:4])[CH3:22]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 10340Sodium CarbonateHCID 200638994-chloroacetyl-9,10-dihydro-4H-thieno[3,4-b][1,5]benzodiazepin-10-one

Product 1

HCID 54567917HCID 54567917, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.0 g of 4-chloroacetyl-9,10-dihydro-4H-thieno[3,4-b][1,5]benzodiazepin-10-one, 6 ml of 40% strength aqueous dimethylamine solution and 10 ml of methylene chloride are stirred at 35° C. for 2 hours; 0.35 g of sodium carbonate is added, and the mixture is concentrated to dryness in vacuo. A little water is added; the solution is extracted repeatedly by shaking it with chloroform, and the organic solution is dried with sodium sulfate and concentrated to dryness. 1.9 g of 4-(dimethylaminoacetyl)-9,10-dihydro-4H-thieno[3,4-b][1,5]benzodiazepin-10-one are thus obtained. 4-(Diethylaminoacetyl)-9,10-dihydro-3-methyl-4H-thieno[3,4-b][1,5]benzodiazepin-10-one [m. 196°-197° C. (from toluene)] is obtained analogously by reacting 4-chloroacetyl-9,10-dihydro-3-methyl-4H-thieno[3,4-b][1,5]benzodiazepin-10-one with a corresponding amount of diethylamine (instead of dimethylamine).

Workup

  1. concentrationthe mixture is concentrated to dryness in vacuo
  2. additionA little water is added
  3. extractionthe solution is extracted repeatedly
  4. dry with materialthe organic solution is dried with sodium sulfate
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-754ee396c36b4e9f95e0a0dcddab5ea2
Source dataset
uspto-grants-1983_04
Patent number
US04381301

Reaction notes

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