Ethylene Oxide → HCID 21823167, compound

HRID 441507Notes

Reaction equation

HRID 441507 reaction equation
C1OC1.C1C2C=CC=CC=2CCON1.[OH:15][CH2:16][CH2:17][N:18]1[O:24][CH2:23][CH2:22][C:21]2[CH:25]=[CH:26][CH:27]=[CH:28][C:20]=2[CH2:19]1.[O-:29][C:30]#[N:31].[Na+]>C(Cl)(Cl)Cl.CO>[C:30]([O:15][CH2:16][CH2:17][N:18]1[O:24][CH2:23][CH2:22][C:21]2[CH:25]=[CH:26][CH:27]=[CH:28][C:20]=2[CH2:19]1)(=[O:29])[NH2:31]

Participants

7

Reactant 4

HCID 6354Ethylene OxideHCID 517096Sodium CyanateHCID 21419189HCID 21419189, compoundHCID 21823166HCID 21823166, compound

Product 1

HCID 21823167HCID 21823167, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

8 Grams of ethylene oxide was dissolved at room temperature in 80 ml. of methanol. To this solution, 8 mg. of 1,2,4,5-tetrahydro-3,2-benzoxazepine were added. After standing overnight, the reaction mixture was refluxed for one hour and then evaporated in vacuo. The residue was distilled at 120° C./0.1 mm Hg. giving 9.3 g. of 2-(2-hydroxyethyl)-1,2,4,5-tetrahydro-3,2-benzoxazepine. To 2.9 g. of the latter compound in 160 ml. of chloroform, 2.47 g. of sodium cyanate was added, then hydrogen chloride was bubbled therethrough for about 30 minutes under stirring. The reaction mixture was then transferred to a separatory funnel and treated with 90 ml. aqueous of 5 percent sodium hydroxide. The organic layer was separated, washed with a saturated solution of sodium chloride and dried over sodium sulfate. After evaporation of the chloroform solution, the residue was crystallized from diisopropyl ether giving 1.82 g. of 2-(2-carbamyloxyethyl)-1,2,4,5-tetrahydro-3,2-benzoxazepine, m.p. 110°-111° C.

Workup

  1. temperaturethe reaction mixture was refluxed for one hour
  2. customevaporated in vacuo
  3. distillationThe residue was distilled at 120° C./0.1 mm Hg
  4. customgiving 9.3 g
  5. customhydrogen chloride was bubbled
  6. customThe reaction mixture was then transferred to a separatory funnel
  7. additiontreated with 90 ml
  8. customThe organic layer was separated
  9. washwashed with a saturated solution of sodium chloride
  10. dry with materialdried over sodium sulfate
  11. customAfter evaporation of the chloroform solution
  12. customthe residue was crystallized from diisopropyl ether giving 1.82 g

Sources & evidence

ORD record
ord-f8cfcb6535da40ff8f8175e8400f2d3a
Source dataset
uspto-grants-1977_08
Patent number
US04041048

Reaction notes

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