Hydrochloric Acid → HCID 89761693, compound

HRID 528661Notes

Reaction equation

HRID 528661 reaction equation
[CH3:1][O:2][C:3]1[CH:38]=[CH:37][C:6]([CH2:7][N:8]([C:32]2[S:33][CH:34]=[CH:35][N:36]=2)[S:9]([C:12]2[CH:13]=[CH:14][C:15]3[N:20]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[O:27]COC)[CH2:19][CH2:18][O:17][C:16]=3[CH:31]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.Cl>C(Cl)Cl.O1CCOCC1>[OH:27][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[N:20]1[CH2:19][CH2:18][O:17][C:16]2[CH:31]=[C:12]([S:9]([N:8]([CH2:7][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:38][CH:37]=3)[C:32]3[S:33][CH:34]=[CH:35][N:36]=3)(=[O:10])=[O:11])[CH:13]=[CH:14][C:15]1=2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 89761916HCID 89761916, compound

Product 1

HCID 89761693HCID 89761693, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of N-(4-methoxybenzyl)-4-(2-(methoxymethoxy)phenyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (600 mg, 2.169 mmol) in DCM (20 mL) was added 20% HCl in 1,4-Dioxane (2.0 mL) at 0° C. The reaction mixture was stirred at ambient temperature for 2 h. After completion, the reaction mixture was quenched with saturated aqueous sodium bicarbonate solution (20 mL) and extracted with DCM (2×20 mL). The organic layer was dried over sodium sulfate and concentrated under reduced pressure to obtain 4-(2-hydroxyphenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide as a yellow solid (550 mg, 99%) which was used for next step without purification.

Workup

  1. customAfter completion, the reaction mixture was quenched with saturated aqueous sodium bicarbonate solution (20 mL)
  2. extractionextracted with DCM (2×20 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b4889c41e32143108c2b6179fb6e5c6c
Source dataset
uspto-grants-2016_05
Patent number
US09346798B2

Reaction notes

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