Sodium Hydroxide → 2,5-Dichloro-3-[(methylsulfonyl)amino]benzoic acid hydrochloride

HRID 1992191노트

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HRID 1992191 반응식
NC1C(Cl)=C(C=C([Cl:12])C=1)C(OC)=O.CCN(C(C)C)C(C)C.CS(Cl)(=O)=O.[Cl:28][C:29]1[C:38]([NH:39][S:40]([CH3:43])(=[O:42])=[O:41])=[CH:37][C:36]([Cl:44])=[CH:35][C:30]=1[C:31]([O:33]C)=[O:32].[OH-].[Na+]>C(Cl)Cl.CO>[ClH:12].[Cl:28][C:29]1[C:38]([NH:39][S:40]([CH3:43])(=[O:41])=[O:42])=[CH:37][C:36]([Cl:44])=[CH:35][C:30]=1[C:31]([OH:33])=[O:32]

참가 물질

8

반응물 5

HCID 14798Sodium HydroxideHCID 23714Chloramben-methyl2회HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 58727879Methyl 2,5-dichloro-3-[(methylsulfonyl)amino]benzoate

생성물 1

HCID 686762592,5-Dichloro-3-[(methylsulfonyl)amino]benzoic acid hydrochloride

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

From common intermediate methyl 3-amino-2,5-dichlorobenzoate following the procedure outlined in scheme. Methyl 3-amino-2,5-dichlorobenzoate (2.10 g, 9.55 mmol), DIEA (3.0 ml) were stirred in DCM (40 ml) at 0° C. methanesulfonyl chloride (2.18 g, 19.08 mmol) was added dropwise whike stirring at 0° C. After 2 hrs at 0° C., reaction was allowed to warm to room temperature while stirring overnight. Quenched rxn with saturated NH4Cl and washed with brine. Organic layer with dried to yield crude methyl 2,5-dichloro-3-[(methylsulfonyl)amino]benzoate (3.10 g) which will be carried on. methyl 2,5-dichloro-3-[(methylsulfonyl)amino]benzoate (3.10 g) was treated with NaOH, methanol following procedure outlined in scheme to form 2,5-dichloro-3-[(methylsulfonyl)amino]benzoic acid hydrochloride (3.53 g).

후처리

  1. additionwas added dropwise
  2. customreaction
  3. temperatureto warm to room temperature
  4. stirringwhile stirring overnight
  5. customQuenched
  6. washwashed with brine
  7. customOrganic layer with dried
  8. customto yield crude methyl 2,5-dichloro-3-[(methylsulfonyl)amino]benzoate (3.10 g) which

출처 및 근거

ORD 기록
ord-9a67d6355e9c4e71bceeabf93228a865
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07645771B2

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