Methyl Ethyl Ketone → HCID 23287875, compound

HRID 1089103Notes

Reaction equation

HRID 1089103 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[O:6][CH2:7][O:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[NH:11][C:4]=2[CH:3]=1.Br[CH2:19][CH2:20][CH2:21][Cl:22].[OH-].[Na+].C(C(C)=O)C>C1C=CC=CC=1>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[O:6][CH2:7][O:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[N:11]([CH2:19][CH2:20][CH2:21][Cl:22])[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 80061-Bromo-3-chloropropaneHCID 14798Sodium Hydroxide2×HCID 13497198HCID 13497198, compound

Product 1

HCID 23287875HCID 23287875, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 14.9 g. (0.06 moles) of 2-chloro-12H-dibenzo[d,g][1,3,6]dioxazocine, 37.8 g. (0.24 moles) of 1-bromo-3-chloropropane, 19.6 g. (0.48 moles) of sodium hydroxide and 180 ml. of methyl ethyl ketone is stirred under reflux for 10 hours. Thereafter further 19.6 g. (0.48 moles) of sodium hydroxide are added and the stirring under reflux continued for 10 hours. The reaction mixture is cooled to 20° C. and poured to 300 g. of broken ice under stirring. 100 ml. of benzene are added, the organic phase is separated and the solvent is removed in vacuo. The residue is subjected to vacuum destillation. There are obtained 14.3 g. of a yellow viscous liquid, b.p./0.3 mmHg: 165° to 171° C. This liquid solidifies upon trituration with petrol ether. Recrystallization from isopropanol affords 12.5 g. (64.0%) of a white product, melting at 105° to 108° C.

Workup

  1. additionA mixture of 14.9 g
  2. temperatureunder reflux for 10 hours
  3. temperaturethe stirring under reflux
  4. additionpoured to 300 g
  5. customthe organic phase is separated
  6. customthe solvent is removed in vacuo
  7. customThere are obtained 14.3 g
  8. custom165° to 171° C
  9. customRecrystallization from isopropanol
  10. customaffords 12.5 g

Sources & evidence

ORD record
ord-2c98db149e8f4f6581cc91520aa71ef3
Source dataset
uspto-grants-1990_10
Patent number
US04965259

Reaction notes

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