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

HRID 1902439Notes

Reaction equation

HRID 1902439 reaction equation
[NH:1]1[C:6]2[CH:7]=[CH:8][S:9][C:5]=2[C:4](=[O:10])[O:3][C:2]1=O.[NH:12]([CH2:14]C(O)=O)[CH3:13]>CS(C)=O.C(OCC)(=O)C>[CH3:13][N:12]1[C:4](=[O:10])[C:5]2[S:9][CH:8]=[CH:7][C:6]=2[NH:1][C:2](=[O:3])[CH2:14]1

Participants

5

Reactant 2

HCID 1088SarcosineHCID 27775521H,2H,4H-thieno(3,2-d)(1,3)oxazine-2,4-dione

Product 1

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

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 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-7ff6431d8e9948f2bae575cdbf3fe2ff
Source dataset
uspto-grants-1982_12
Patent number
US04363762

Reaction notes

Loading…