Ammonium Chloride → HCID 86731296, compound

HRID 2277226Notes

Reaction equation

HRID 2277226 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:13]2[O:14][C:15]3[CH2:21][CH:20]([OH:22])[CH2:19][CH2:18][C:16]=3[N:17]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH:10]1[CH2:12][CH2:11]1.Cl[CH2:24][C:25]([N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1)=[O:26].CC(C)([O-])C.[K+].[Cl-].[NH4+]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:13]2[O:14][C:15]3[CH2:21][CH:20]([O:22][CH2:24][C:25]([N:27]4[CH2:32][CH2:31][O:30][CH2:29][CH2:28]4)=[O:26])[CH2:19][CH2:18][C:16]=3[N:17]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH:10]1[CH2:11][CH2:12]1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 74040Morpholine, 4-(chloroacetyl)-HCID 23665647Potassium tert-butoxideHCID 86731295HCID 86731295, compound

Product 1

HCID 86731296HCID 86731296, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(3-chloro-4-(cyclopropylmethoxy)phenyl)-4,5,6,7-tetrahydro-1,3-benzoxazol-6-ol (6.61 g) and 4-(chloroacetyl)morpholine (5.38 mL) in THF (50 mL) was added potassium tert-butoxide (4.64 g), and the mixture was stirred for 1 hr under a nitrogen stream. To the reaction mixture was added saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate/methanol) to give the title compound (9.24 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate/methanol)

Sources & evidence

ORD record
ord-6b0028ae4f6a4b80827b5310e23c13a9
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

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