Sulfuric Acid → N-(2-(cyclopropylmethoxy)-4-mercaptophenyl)methanesulfonamide

HRID 1776480Notes

Reaction equation

HRID 1776480 reaction equation
C([S:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][S:14]([CH3:17])(=[O:16])=[O:15])=[C:9]([O:18][CH2:19][CH:20]2[CH2:22][CH2:21]2)[CH:8]=1)(=S)OCC.[OH-].[K+].[BH4-].[Na+].OS(O)(=O)=O>CO.O.CCOC(C)=O>[CH:20]1([CH2:19][O:18][C:9]2[CH:8]=[C:7]([SH:6])[CH:12]=[CH:11][C:10]=2[NH:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH2:21][CH2:22]1

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 14797Potassium HydroxideHCID 4311764Sodium borohydride2×HCID 86679433S-3-(cyclopropylmethoxy)-4-(methylsulfonamido)-phenyl O-ethyl carbonodithioate

Product 1

HCID 86679432N-(2-(cyclopropylmethoxy)-4-mercaptophenyl)methanesulfonamideYield 32.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of crude S-3-(cyclopropylmethoxy)-4-(methylsulfonamido)-phenyl O-ethyl carbonodithioate (prepared as described in Step 7, 0.903 g, 2.497 mmol) in MeOH (15 ml), KOH (0.392 g, 6.99 mmol) was added followed by NaBH4 (0.071 g, 1.873 mmol), and the mixture was stirred at RT for 1 hour. NaBH4 (0.047 g, 1.249 mmol) was freshly added, and the mixture was stirred at RT for 1 hour. Then the mixture was acidified with 10% H2SO4 (until effervescence ceased). The residue was portioned between EtOAc and water, and the organic layer was washed with water, dried over na2SO4 and evaporated. The residue was purified by flash chromatography on silica gel cartridge (DCM:EtOAc=80:20) affording N-(2-(cyclopropylmethoxy)-4-mercaptophenyl)methanesulfonamide (0.222 g, 0.812 mmol, 32.5% yield, MS/ESI+ 295.9 [MNa]+).

Workup

  1. stirringthe mixture was stirred at RT for 1 hour
  2. washthe organic layer was washed with water
  3. customdried over na2SO4
  4. customevaporated
  5. customThe residue was purified by flash chromatography on silica gel cartridge (DCM:EtOAc=80:20)

Sources & evidence

ORD record
ord-add91cff9ed14c3184e2ff2486dc2c04
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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