Formic Acid → 2-Bromo-6-(sulfamoylamino)naphthalene

HRID 2378555Notes

Reaction equation

HRID 2378555 reaction equation
Cl[S:2]([N:5]=C=O)(=[O:4])=[O:3].C(O)=O.[NH2:11][C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([Br:22])[CH:18]=2)[CH:13]=1.C(OCC)(=O)C>C1C=CC=CC=1>[Br:22][C:17]1[CH:16]=[CH:15][C:14]2[C:19](=[CH:20][CH:21]=[C:12]([NH:11][S:2](=[O:4])(=[O:3])[NH2:5])[CH:13]=2)[CH:18]=1

Participants

6

Reactant 4

HCID 284Formic AcidHCID 8857Ethyl AcetateHCID 70918Chlorosulfonyl isocyanateHCID 3484042-Amino-6-bromonaphthalene

Product 1

HCID 225590432-Bromo-6-(sulfamoylamino)naphthalene

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of chlorosulfonyl isocyanate (870 μl, WAKO) in benzene (10 ml) was added dropwise with formic acid (377 μl, WAKO) under ice cooling, warmed to room temperature, stirred and for 19.5 hours, then warmed to 40° C., and further stirred for 4 hours. The reaction mixture was added dropwise with a solution of 2-amino-6-bromonaphthalene (443 mg) in benzene (5 ml) under ice cooling, warmed to room temperature, and stirred 21.5 hours. The reaction mixture was filtered to obtain solid, and the solid was added with ethyl acetate, mixed and filtered again. The solvent of the filtrate was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=2:1) to obtain the title compound (Intermediate 66, 158 mg).

Workup

  1. temperaturewarmed to 40° C.
  2. stirringfurther stirred for 4 hours
  3. temperaturewarmed to room temperature
  4. stirringstirred 21.5 hours
  5. filtrationThe reaction mixture was filtered
  6. customto obtain solid
  7. additionmixed
  8. filtrationfiltered again
  9. customThe solvent of the filtrate was evaporated under reduced pressure
  10. customThe residue was purified by column chromatography (Quad, hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-439009b9cbc64135ae37ed1c7f5f3d8d
Source dataset
uspto-grants-2008_12
Patent number
US07470807B2

Reaction notes

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