Dimethyl Sulfate → HCID 20364766, compound

HRID 1973296Notes

Reaction equation

HRID 1973296 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[NH:13][C:12](=[O:20])[CH2:11][N:10]=2)[CH:4]=1.[CH3:23]OS(OC)(=O)=O>CC(C)=O>[CH3:23][N:13]1[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:9]([C:5]2[CH:4]=[C:3]([C:2]([F:1])([F:21])[F:22])[CH:8]=[CH:7][CH:6]=2)=[N:10][CH2:11][C:12]1=[O:20]

Participants

4

Reactant 2

HCID 6497Dimethyl SulfateHCID 23275906HCID 23275906, compound

Product 1

HCID 20364766HCID 20364766, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 15.2 g. of 1,3-dihydro-5-(α,α,α-trifluoro-m-tolyl)-2H-1,4-benzodiazepin-2-one in 360ml. of acetone is treated with 7.5 ml. of dimethylsulfate and 45 g. of finely triturated, dry potassium carbonate and stirred intensively at room temperature for 15 hours. The mixture is then poured into 400 ml. of ice-water, the acetone is evaporated under reduced pressure and the separated oil extracted with methylene chloride. The extract is washed with water, dried over sodium sulfate and evaporated to dryness. The resulting oil crystallizes on trituration with hexane, and there is obtained 1,3-dihydro-1-methyl-5-(α,α,α-trifluoro-m-tolyl)-2H-1,4-benzodiazepin-2-one having a melting point of 117°-119° C., which can be employed in the next stage without further purification. A sample for analysis is obtained by crystallization from ethanol; melting point 121°-122° C.

Workup

  1. customof finely triturated
  2. additionThe mixture is then poured into 400 ml
  3. customof ice-water, the acetone is evaporated under reduced pressure
  4. extractionthe separated oil extracted with methylene chloride
  5. washThe extract is washed with water
  6. dry with materialdried over sodium sulfate
  7. customevaporated to dryness
  8. customThe resulting oil crystallizes on trituration with hexane

Sources & evidence

ORD record
ord-55f63a5b018841489191afe06533bfcc
Source dataset
uspto-grants-1976_12
Patent number
US03996374

Reaction notes

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