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

HRID 2378555

반응식

HRID 2378555 반응식
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

참가 물질

6

반응물 4

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

생성물 1

HCID 225590432-Bromo-6-(sulfamoylamino)naphthalene

시약·촉매·용매 1

HCID 241Benzene용매2회

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-439009b9cbc64135ae37ed1c7f5f3d8d
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07470807B2

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