Cloxazolam → HCID 21442401, compound

HRID 328493Notes

Reaction equation

HRID 328493 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=[O:12])[CH2:9][N:8]3[CH2:13][CH2:14][O:15][C:7]3([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:22])[C:6]=2[CH:23]=1.C[O-].[Na+].[CH3:27][O:28][CH2:29]Cl>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH2:27][O:28][CH3:29])[C:10](=[O:12])[CH2:9][N:8]3[CH2:13][CH2:14][O:15][C:7]3([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:22])[C:6]=2[CH:23]=1

Participants

5

Reactant 3

HCID 2816CloxazolamHCID 7864Chloromethyl Methyl EtherHCID 10942334Sodium Methoxide

Product 1

HCID 21442401HCID 21442401, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2.8 g. of 10-chloro-11b-(2-chlorophenyl)-2,3,5,11b-tetrahydrooxazolo[3,2-d][1,4]benzodiazepin-6(7H)-one in 50 ml. of dimethylformamide was cooled to -10° and treated with 0.65 g. of sodium methoxide. After stirring for 5 minutes, the mixture was cooled to -40° and 1 ml. of chlorodimethyl ether was added. The cooling bath was removed and when the temperature had reached 0° the reaction mixture was poured into 300 ml. of ice-water. The precipitated material was collected by suction and dissolved in methylene chloride. The solution was dried over sodium sulfate, filtered and evaporated. The residue was crystallized from a mixture of ether and hexane to give, after recrystallization from ethanol, 10-chloro-11b-(2-chlorophenyl)-7-methoxymethyl-2,3,5,11b-tetrahydrooxazolo[3,2-d][1,4]benzodiazepin-6(7H)-one as white prisms, m.p. 144°-147°.

Workup

  1. additiontreated with 0.65 g
  2. temperaturethe mixture was cooled to -40°
  3. customThe cooling bath was removed
  4. customhad reached 0°
  5. additionwas poured into 300 ml
  6. customThe precipitated material was collected by suction
  7. dissolutiondissolved in methylene chloride
  8. dry with materialThe solution was dried over sodium sulfate
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue was crystallized from a mixture of ether and hexane
  12. customto give
  13. customafter recrystallization from ethanol, 10-chloro-11b-(2-chlorophenyl)-7-methoxymethyl-2,3,5,11b-tetrahydrooxazolo[3,2-d][1,4]benzodiazepin-6(7H)-one as white prisms, m.p. 144°-147°

Sources & evidence

ORD record
ord-fad6875705c1478a8e0c8880e0c0fd54
Source dataset
uspto-grants-1977_04
Patent number
US04017532

Reaction notes

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