Triethylamine → 3-methyl-4-(n-butanesulfonamido)phenyl N-methylcarbamate

HRID 2072425Notes

Reaction equation

HRID 2072425 reaction equation
[CH2:1]([S:5](Cl)(=[O:7])=[O:6])[CH2:2][CH2:3][CH3:4].[CH3:9][NH:10][C:11](=[O:21])[O:12][C:13]1[CH:18]=[CH:17][C:16]([NH2:19])=[C:15]([CH3:20])[CH:14]=1.C(N(CC)CC)C>C1C=CC=CC=1>[CH3:9][NH:10][C:11](=[O:21])[O:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][S:5]([CH2:1][CH2:2][CH2:3][CH3:4])(=[O:7])=[O:6])=[C:15]([CH3:20])[CH:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 25072AminomatacilHCID 754301-Butanesulfonyl chloride

Product 1

HCID 537524853-methyl-4-(n-butanesulfonamido)phenyl N-methylcarbamate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Butanesulfonyl chloride (2.6g., 0.017 mole) was added dropwise to a mixture of 3-methyl-4-aminophenyl N-methylcarbamate (3.0g., 0.017 mole), triethylamine (1.85g., 0.018 mole) and benzene (50 ml.). After refluxing for two hours, the reaction mixture was washed in a separatory funnel with water. The organic phase was dried with anhydrous magnesium sulfate and upon removal of the solvent the product was isolated as a dark oil (3.15g.).

Workup

  1. temperatureAfter refluxing for two hours
  2. washthe reaction mixture was washed in a separatory funnel with water
  3. dry with materialThe organic phase was dried with anhydrous magnesium sulfate and upon removal of the solvent the product
  4. customwas isolated as a dark oil (3.15g.)

Sources & evidence

ORD record
ord-d9e0a60505e64b8f87cc309ab62176c9
Source dataset
uspto-grants-1977_09
Patent number
US04051254

Reaction notes

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