Ammonia → 2-Methyl-4-benzothiazolesulfonamide

HRID 620117Notes

Reaction equation

HRID 620117 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[C:5](=[C:7]([S:11](Cl)(=[O:13])=[O:12])[CH:8]=[CH:9][CH:10]=2)[N:6]=1.[NH3:15]>O1CCCC1>[CH3:1][C:2]1[S:3][C:4]2[C:5](=[C:7]([S:11]([NH2:15])(=[O:13])=[O:12])[CH:8]=[CH:9][CH:10]=2)[N:6]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 138244252-Methylbenzo[d]thiazole-4-sulfonyl chloride

Product 1

HCID 138244262-Methyl-4-benzothiazolesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 18 g of the product from Example 1 in 170 mL of tetrahydrofuran was cooled to 0° C. under an atmosphere of nitrogen and treated with 5 mL of anhydrous ammonia. The mixture was stirred at room temperature for about an hour, filtered to remove the ammonium chloride, and the filtrate concentrated in vacuo to give an off-white solid. This crude product was purified by silica gel chromatography; elution with ethyl acetate-hexanes (3:1) gave 1.9 g of 2-methyl-4-benzothiazolesulfonamide as a white powder, m.p. 236°-239° C.; NMR (DMSO-d6 /CDCl3): δ 2.95 (3H, s), 7.0 (2H, br s, SO2NH2), 7.55 (1H, t, J=8 Hz), 8.0 (1H, dd, J=2, 8 Hz), 8.2 (1H, dd, J=2, 8 Hz).

Workup

  1. filtrationfiltered
  2. customto remove the ammonium chloride
  3. concentrationthe filtrate concentrated in vacuo
  4. customto give an off-white solid
  5. customThis crude product was purified by silica gel chromatography
  6. washelution with ethyl acetate-hexanes (3:1)

Sources & evidence

ORD record
ord-a45909677d9648b0ba38ad289718cdb5
Source dataset
uspto-grants-1989_04
Patent number
US04820332

Reaction notes

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