Methylamine → HCID 68153613, compound

HRID 1405370Notes

Reaction equation

HRID 1405370 reaction equation
Cl[S:2]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][C:6]=1[CH3:14])(=[O:4])=[O:3].CN.[CH2:17]([N:19](CC)CC)C>>[CH3:14][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][C:5]=1[S:2](=[O:4])(=[O:3])[NH:19][CH3:17])[C:9]([OH:11])=[O:10]

Participants

4

Reactant 3

HCID 6329MethylamineHCID 8471TriethylamineHCID 552795631314960-92-3

Product 1

HCID 68153613HCID 68153613, compoundYield 87.3%

Procedure

4-Chlorosulfonyl-3-methyl-benzoic acid (0.99 g, 4.2 mmol), methanamine (2.0 mL of 33% w/v, 21 mmol), and triethylamine (1.8 mL, 13 mmol) were stirred for 45 min at rt. The reaction mixture was evaporated and the resultant oil was partitioned between ethyl acetate and 1N HCl. The organics were separated and washed with another portion of 1N HCl and then brine. The organics were dried over sodium sulfate and evaporated to give 3-methyl-4-(methylsulfamoyl)benzoic acid (841 mg, 87%). ESI-MS m/z calc. 229.0, found 230.5 (M+1)+; Retention time: 0.64 minutes (3 min run).

Workup

  1. customThe reaction mixture was evaporated
  2. customthe resultant oil was partitioned between ethyl acetate and 1N HCl
  3. customThe organics were separated
  4. washwashed with another portion of 1N HCl
  5. dry with materialThe organics were dried over sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-0c1b2cab12114878bc0e904d54118e93
Source dataset
uspto-grants-2014_12
Patent number
US08916565B2

Reaction notes

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