Triethylamine → 3-methyl-4-(methanesulfonamido)phenyl N-methylcarbamate

HRID 2072422Notes

Reaction equation

HRID 2072422 reaction equation
[CH3:1][NH:2][C:3](=[O:13])[O:4][C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[C:7]([CH3:12])[CH:6]=1.C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>C1C=CC=CC=1>[CH3:1][NH:2][C:3](=[O:13])[O:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][S:22]([CH3:21])(=[O:24])=[O:23])=[C:7]([CH3:12])[CH:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 25072AminomatacilHCID 31297Methanesulfonyl chloride

Product 1

HCID 214093123-methyl-4-(methanesulfonamido)phenyl N-methylcarbamate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A flask was charged with 3-methyl-4-aminophenyl N-methylcarbamate (3.0g., 0.0166 mole), triethylamine (1.83g., 0.018 mole, 2.53 ml.) and about 100 ml. of benzene. To this slurry was added methanesulfonyl chloride and after one hour at reflux the mixture was cooled and filtered. The solids were stirred vigorously with water to dissolve any residual by-product triethylamine hydrochloride. Refiltration and drying gave 2.3g. of the desired product (m.p. 167°-69° C.).

Workup

  1. temperatureafter one hour at reflux the mixture
  2. temperaturewas cooled
  3. filtrationfiltered
  4. dissolutionto dissolve any residual by-product triethylamine hydrochloride
  5. customRefiltration and drying
  6. customgave 2.3g

Sources & evidence

ORD record
ord-24181135411a42c3a879bb8b177c34a6
Source dataset
uspto-grants-1977_09
Patent number
US04051254

Reaction notes

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