Tetrahydrofuran → HCID 89761787, compound

HRID 528526Notes

Reaction equation

HRID 528526 reaction equation
[O:1]1[CH2:6][CH2:5][NH:4][C:3]2[CH:7]=[CH:8][C:9]([S:11](Cl)(=[O:13])=[O:12])=[CH:10][C:2]1=2.[S:15]1[C:19]([NH2:20])=[N:18][CH:17]=[N:16]1.C1COCC1.[OH-].[Na+]>Cl>[S:15]1[C:19]([NH:20][S:11]([C:9]2[CH:8]=[CH:7][C:3]3[NH:4][CH2:5][CH2:6][O:1][C:2]=3[CH:10]=2)(=[O:13])=[O:12])=[N:18][CH:17]=[N:16]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 2902745-Amino-1,2,4-thiadiazoleHCID 573469673,4-Dihydro-2H-1,4-benzoxazine-7-sulfonyl chloride

Product 1

HCID 89761787HCID 89761787, compoundYield 34.9%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A vial was charged with 3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonyl chloride (from HangZhou Trylead Chemical, Hangzhou, China) (74.42 mg, 0.318 mmol), 1,2,4-thiadiazol-5-amine (70.9 mg, 0.701 mmol), and THF (1991 μL) to give a cloudy solution. The vial was cooled in an ice-bath for 5 min, then sodium hydroxide (6N aq.) (117 μL, 0.701 mmol) was added dropwise. After 45 min, the mixture was allowed to warm to room temperature with the bath. The mixture was diluted with 1N aq. HCl and extracted with EtOAc (3×). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated. The residue was purified by chromatography on silica gel (4% MeOH/DCM). Several mixed fractions at the tail end of the elution were discarded, and the remainder that contained product were combined and concentrated to give N-(1,2,4-thiadiazol-5-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (33.19 mg, 0.111 mmol) as a white foam. m/z (ESI) 299.2 (M+H)+.

Workup

  1. customto give a cloudy solution
  2. temperatureThe vial was cooled in an ice-bath for 5 min
  3. extractionextracted with EtOAc (3×)
  4. dry with materialThe combined organic extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on silica gel (4% MeOH/DCM)
  8. additionSeveral mixed fractions
  9. washat the tail end of the elution
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-b560cec318b0454db5338903a62938e4
Source dataset
uspto-grants-2016_05
Patent number
US09346798B2

Reaction notes

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