Benzenesulfonyl chloride → HCID 68296418, compound

HRID 631880Notes

Reaction equation

HRID 631880 reaction equation
[CH2:1]([N:8]1[C:12]([C:13]2[C:18]([O:19][CH3:20])=[CH:17][CH:16]=[CH:15][C:14]=2[NH2:21])=[N:11][N:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22]1([S:28](Cl)(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>N1C=CC=CC=1.C(Cl)Cl>[CH2:1]([N:8]1[C:12]([C:13]2[C:18]([O:19][CH3:20])=[CH:17][CH:16]=[CH:15][C:14]=2[NH:21][S:28]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:30])=[O:29])=[N:11][N:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 68296409HCID 68296409, compound2×

Product 1

HCID 68296418HCID 68296418, compoundYield 63.8%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

2-(1-Benzyl-1H-tetrazol-5-yl)-3-methoxyphenylamine (Intermediate 13, 0.115 g) was dissolved in pyridine (0.16 mL) and DCM (2 mL). Benzenesulfonyl chloride (0.08 g) was added and the mixture was stirred overnight. The reaction mixture was diluted with DCM and washed with 1N hydrochloric acid, dried with magnesium sulfate and filtered. The filtrate was evaporated to dryness and the residue was purified by flash chromatography on silica, eluting with a mixture of DCM and methanol. The fractions containing the desired product were combined and evaporated to give the title compound as a colorless solid (0.11 g).

Workup

  1. washwashed with 1N hydrochloric acid
  2. dry with materialdried with magnesium sulfate
  3. filtrationfiltered
  4. customThe filtrate was evaporated to dryness
  5. customthe residue was purified by flash chromatography on silica
  6. washeluting with a mixture of DCM and methanol
  7. additionThe fractions containing the desired product
  8. customevaporated

Sources & evidence

ORD record
ord-182264c5fe034d749087b36ba9be7f97
Source dataset
uspto-grants-2016_04
Patent number
US09321740B2

Reaction notes

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