Water → HCID 57961739, compound

HRID 541911Notes

Reaction equation

HRID 541911 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([SH:8])[CH:5]=[CH:6][CH:7]=1.C[O-].[Na+].Br[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=1.O>CN(C)C=O>[N+:20]([C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=1)[CH2:13][S:8][C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[NH2:1])([O-:22])=[O:21]

Participants

6

Reactant 4

HCID 962WaterHCID 315773-AminothiophenolHCID 77568Benzene, 1-(bromomethyl)-3-nitro-HCID 10942334Sodium Methoxide

Product 1

HCID 57961739HCID 57961739, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of 3-aminobenzenethiol (0.51 mL, 4.8 mmol) and sodium methoxide (0.31 g, 5.8 mmol) in N,N-dimethylformamide (5.3 mL) was stirred at 25° C. for 10 minutes (min). The reaction mixture was treated with a solution of 1-(bromomethyl)-3-nitro-benzene (1.0 g, 4.8 mmol) in N,N-dimethylformamide (4.5 mL) dropwise and stirred at 25° C. for 1 h. The reaction mixture was poured into water (50 mL) and extracted with ethyl acetate (100 mL). The organic layer was separated and washed with brine (25 mL), dried over anhydrous sodium sulfate, filtered, and evaporated to give a crude brown oil. This material was purified by flash column chromatography to give the desired product (1.2 g, 95%) as a tan oil. LCMS for C13H13N2O2S (M+H)+: m/z=261.0.

Workup

  1. extractionextracted with ethyl acetate (100 mL)
  2. customThe organic layer was separated
  3. washwashed with brine (25 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto give a crude brown oil
  8. customThis material was purified by flash column chromatography

Sources & evidence

ORD record
ord-ae40c2a4988a4701bea9b95d3f0f6a31
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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