Formic Acid → N-tert-Butyl-5-formylamino-2-methoxycarbonylbenzenesulfonamide

HRID 998

반응식

HRID 998 반응식
[CH:1](O)=[O:2].C(OC(=O)C)(=O)C.[C:11]([NH:15][S:16]([C:19]1[CH:24]=[C:23]([NH2:25])[CH:22]=[CH:21][C:20]=1[C:26]([O:28][CH3:29])=[O:27])(=[O:18])=[O:17])([CH3:14])([CH3:13])[CH3:12]>CN(C=O)C>[C:11]([NH:15][S:16]([C:19]1[CH:24]=[C:23]([NH:25][CH:1]=[O:2])[CH:22]=[CH:21][C:20]=1[C:26]([O:28][CH3:29])=[O:27])(=[O:18])=[O:17])([CH3:14])([CH3:13])[CH3:12]

참가 물질

5

반응물 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 10946074methyl 4-amino-2-(N-tert-butylsulfamoyl)benzoate

생성물 1

HCID 19693794N-tert-Butyl-5-formylamino-2-methoxycarbonylbenzenesulfonamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

6.5 ml of formic acid are carefully added at 0° C. to 13 ml of acetic anhydride. The mixture is subsequently heated at 50°-60° C. for 2 h. A solution of 16.0 g (0.056 mol) of N-tert-butyl-5-amino-2-methoxycarbonylbenzenesulfonamide in 50 ml of DMF is then added dropwise at 0° C. The cooling bath is removed and the mixture is stirred for a further 4 h at room temperature. The reaction mixture is then shaken up in 800 ml of ethyl acetate and washed with three times 150 ml of water. The organic phase is dried over magnesium sulfate, the solvent is distilled off, and the residue is recrystallized from ethyl acetate/n-heptane. The product is N-tert-butyl-5-formylamino-2-methoxycarbonylbenzenesulfonamide (14.23 g, 82% of theory) which melts at 113°-114° C.

후처리

  1. temperatureThe mixture is subsequently heated at 50°-60° C. for 2 h
  2. customThe cooling bath is removed
  3. stirringThe reaction mixture is then shaken up in 800 ml of ethyl acetate
  4. washwashed with three times 150 ml of water
  5. dry with materialThe organic phase is dried over magnesium sulfate
  6. distillationthe solvent is distilled off
  7. customthe residue is recrystallized from ethyl acetate/n-heptane

출처 및 근거

ORD 기록
ord-e6119d1ed5fd4cad8ff5deeb55d6be7b
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05723409

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