Chlorosulfonic acid → HCID 59656534, compound

HRID 561296Notes

Reaction equation

HRID 561296 reaction equation
[CH3:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[C:4]([NH:6][C:7]1[C:16]2[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=2[CH:10]=[CH:9][CH:8]=1)=[O:5].Cl[S:22]([OH:25])(=[O:24])=[O:23]>C(O)(C(F)(F)F)=O>[CH3:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[C:4]([NH:6][C:7]1[C:16]2[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=2[C:10]([S:22]([OH:25])(=[O:24])=[O:23])=[CH:9][CH:8]=1)=[O:5]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 796063Benzamide, 2-methyl-N-(5,6,7,8-tetrahydro-1-naphthalenyl)-

Product 1

HCID 59656534HCID 59656534, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
25 °C

Procedure

To a 0° C. solution of amide (22) in TFA (1 mL per mmol amide), was added chlorosulfonic acid (2 eq) dropwise under nitrogen atmosphere. The temperature was allowed to warm to 25° C. and stirred for 72 hours. The reaction mixture was quenched by pouring into ice water. The desired product was collected via precipitation from either water/methanol, or ethyl acetate/methanol solution, resulting in a white solid (yield 68%). LC/MS (M+H)+ m/z 346, (M−H)− m/z 344. The crude material was used without further purification.

Workup

  1. customThe reaction mixture was quenched
  2. additionby pouring into ice water
  3. customThe desired product was collected via precipitation from either water/methanol, or ethyl acetate/methanol solution

Sources & evidence

ORD record
ord-242f6c06b8df4d45912f2f9c64cb6e18
Source dataset
uspto-grants-2011_11
Patent number
US08063222B2

Reaction notes

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