Ethyl chloroformate → HCID 19871144, compound

HRID 329726Notes

Reaction equation

HRID 329726 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:16]([OH:18])=O)[C:5]2[O:10][CH:9]([CH3:11])[C:8](=[O:12])[N:7]([CH2:13][CH3:14])[C:6]=2[CH:15]=1.C(Cl)(=O)OCC.[NH2:25][CH:26]1[CH:31]2[CH2:32][CH2:33][N:28]([CH2:29][CH2:30]2)[CH2:27]1.C(=O)([O-])O.[Na+]>O1CCCC1.C(OCC)(=O)C.C(N(CC)CC)C>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([C:16]([NH:25][CH:26]2[CH:31]3[CH2:32][CH2:33][N:28]([CH2:29][CH2:30]3)[CH2:27]2)=[O:18])[C:5]2[O:10][CH:9]([CH3:11])[C:8](=[O:12])[N:7]([CH2:13][CH3:14])[C:6]=2[CH:15]=1

Participants

8

Reactant 4

HCID 10928Ethyl chloroformateHCID 1232383-AminoquinuclidineHCID 516892Sodium BicarbonateHCID 14802116HCID 14802116, compound

Product 1

HCID 19871144HCID 19871144, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4.2 g of 6-chloro-4-ethyl-3,4-dihydro-2-methyl-3-oxo-2H-1,4-benzoxazine-8-carboxylic acid in 100 ml of tetrahydrofuran is cooled to below 0° C. and 5 ml of triethylamine is added under stirring thereto. Further, 2.0 g of ethyl chlorocarbonate is added and the mixture is stirred for 30 minutes. To the resultant mixture is added 3.0 g of 3-aminoquinuclidine and the mixture stirred for 5 hours. After completion of the reaction, aqueous sodium hydrogen carbonate and ethyl acetate are added. The organic layer is separated, washed with water and dried over magnesium sulfate. The solvent is distilled off and the residue is converted into the corresponding hydrochloride by treating with ethanolic hydrochloric acid followed by recrystallizing from ethanol-ethyl acetate to give 6-chloro-4-ethyl-3,4-dihydro-2-methyl-3-oxo-N-(3-quinuclidinyl)-2H-1,4-benzoxazine-8-carboxamide hydrochloride, melting at 249°-252° C.

Workup

  1. stirringthe mixture is stirred for 30 minutes
  2. stirringthe mixture stirred for 5 hours
  3. additionare added
  4. customThe organic layer is separated
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. distillationThe solvent is distilled off
  8. additionby treating with ethanolic hydrochloric acid
  9. customby recrystallizing from ethanol-ethyl acetate

Sources & evidence

ORD record
ord-6098f3a0a69d4231815c95412b6d173f
Source dataset
uspto-grants-1990_01
Patent number
US04892872

Reaction notes

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