Formic Acid → HCID 22559043, compound

HRID 984707

Reaction equation

HRID 984707 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>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

5

Reactant 3

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

Product 1

HCID 22559043HCID 22559043, compound

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 for 19.5 hours, then heated to 40° C. and further stirred for 4 hours. The reaction mixture was added dropwise with a solution (5 ml) of 2-amino-6-bromonaphthalene (443 mg) in benzene under ice cooling, warmed to room temperature and stirred for 21.5 hours. The reaction mixture was filtered, and the obtained solid was added with ethyl acetate and mixed. The mixture was filtered again, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=2:1) to obtain the title compound (Intermediate 28, 158 mg).

Workup

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

Sources & evidence

ORD record
ord-a3cb2ca8d20d416a9157656051eb274a
Source dataset
uspto-grants-2005_03
Patent number
US06867320B2

Linked notes

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