Dimethyl Sulfoxide → 4-Methyl-3,4-dihydro-1H-thieno[3,2-e][1,4]diazepine-2,5-dione

HRID 67527Notes

Reaction equation

HRID 67527 reaction equation
[N:1]1[CH2:2][O:3][CH:4]=[C:5]2[S:9][CH:8]=[CH:7][C:6]=12.[NH:10]([CH2:12]C(O)=O)[CH3:11].CS(C)=[O:18]>C(OCC)(=O)C>[CH3:11][N:10]1[C:4](=[O:3])[C:5]2[S:9][CH:8]=[CH:7][C:6]=2[NH:1][C:2](=[O:18])[CH2:12]1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 1088SarcosineHCID 867385412H-thieno[3,2-d][1,3]oxazine

Product 1

HCID 538457174-Methyl-3,4-dihydro-1H-thieno[3,2-e][1,4]diazepine-2,5-dione

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 30.0 g (177 mmol) of 2H-thieno[3,2-d][1,3]oxazine-2,4(1H-dione and 17.3 g (195 mmol) of sarcosine in 100 ml of dimethyl sulphoxide is stirred at 110° C. for 1.5 hours. The dark brown coloured solution is poured into ca 600 ml of ice/water. The separated oil is taken up in ca 200 ml of ethyl acetate and the aqueous phase is evaporated in vacuo until crystallisation begins. The mixture is cooled in an ice-bath for ca 3 hours and the separated material is filtered off under suction and washed with a small amount of water. After drying on a rotary evaporator, there is obtained 3,4-dihydro-4-methyl-2H-thieno[3,2-e][1,4]diazepine-2,5(1H)-dione of melting point 270°-272° C.

Workup

  1. customthe aqueous phase is evaporated in vacuo until crystallisation
  2. temperatureThe mixture is cooled in an ice-bath for ca 3 hours
  3. filtrationthe separated material is filtered off under suction
  4. washwashed with a small amount of water
  5. customAfter drying on a rotary evaporator

Sources & evidence

ORD record
ord-dcc590cbd7d74fe881ed37f5de0a6ea2
Source dataset
uspto-grants-1982_08
Patent number
US04346033

Reaction notes

Loading…