Chlorosuccinimide → HCID 178449970, compound

HRID 1484987Notes

Reaction equation

HRID 1484987 reaction equation
[C:1]([NH:5][S:6]([C:9]1[S:10][C:11]([C:14]2[N:19]=[C:18]([CH:20]3[CH2:22][CH2:21]3)[CH:17]=[C:16]([OH:23])[N:15]=2)=[CH:12][CH:13]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C(=O)N([Cl:31])C(=O)C1>C(O)(=O)C>[C:1]([NH:5][S:6]([C:9]1[S:10][C:11]([C:14]2[N:19]=[C:18]([CH:20]3[CH2:22][CH2:21]3)[C:17]([Cl:31])=[C:16]([OH:23])[N:15]=2)=[CH:12][CH:13]=1)(=[O:7])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 178449969HCID 178449969, compound

Product 1

HCID 178449970HCID 178449970, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of N-tert-butyl-5-(4-cyclopropyl-6-hydroxypyrimidin-2-yl)thiophene-2-sulfonamide (353 mg, 1.0 mmol) and NCS (139 mg, 1.05 mmol, 1.0 equiv.) in acetic acid (5 mL) was stirred at rt for 1 h. The reaction was extracted with EA, the organic layer was washed with (brine), dried (Na2SO4) and concentrated to provide N-tert-butyl-5-(5-chloro-4-cyclopropyl-6-hydroxypyrimidin-2-yl)thiophene-2-sulfonamide (341 mg, 88%). LC-MS (m/z)=388.1 [M+H]+

Workup

  1. extractionThe reaction was extracted with EA
  2. washthe organic layer was washed with (brine)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3fe987d142244597b6f6674efb07165a
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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