Dimethyl Sulfoxide → HCID 12448362, compound

HRID 1287567Notes

Reaction equation

HRID 1287567 reaction equation
[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=O.[F:9][C:10]1[CH:22]=[C:14]2[C:15](O[C:18](=O)[N:19](C)[C:13]2=[CH:12][CH:11]=1)=[O:16].CS(C)=O>O>[F:9][C:10]1[CH:11]=[CH:12][C:13]2[N:19]([CH3:18])[C:3](=[O:5])[CH:2]3[CH2:6][CH2:7][CH2:8][N:1]3[C:15](=[O:16])[C:14]=2[CH:22]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 145742L-ProlineHCID 127132306-Fluoro-1-methyl-2H-3,1-benzoxazine-2,4(1H)-dione

Product 1

HCID 12448362HCID 12448362, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6.2 g. of L-proline, 10.0 g. of 5-fluoro-N-methylisatoic anhydride and 30 ml. of dimethyl sulfoxide is heated on a steam bath for 6 hours, cooled and then diluted with 100 ml. of water. The reaction mixture is evaporated with benzene and the benzene layer is washed twice with water and concentrated. The residue is dissolved in ether and cooled. The crystals are filtered off and dried in a vacuum oven. The dextrorotatory 7-fluoro-1,2,3,11a-tetrahydro-10-methyl-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5,11(10H)dione melts at 131°-132°, [α]D25 + 417° (1.6%, methanol).

Workup

  1. additionA mixture of 6.2 g
  2. temperaturecooled
  3. additiondiluted with 100 ml
  4. customThe reaction mixture is evaporated with benzene
  5. washthe benzene layer is washed twice with water
  6. concentrationconcentrated
  7. dissolutionThe residue is dissolved in ether
  8. temperaturecooled
  9. filtrationThe crystals are filtered off
  10. customdried in a vacuum oven
  11. customThe dextrorotatory 7-fluoro-1,2,3,11a-tetrahydro-10-methyl-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5,11(10H)dione melts at 131°-132°, [α]D25 + 417° (1.6%, methanol)

Sources & evidence

ORD record
ord-5e24f227660d410c876b1b55e638b8c1
Source dataset
uspto-grants-1976_10
Patent number
US03985732

Reaction notes

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