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Toluene → Sulfamic Acid 4-{3-[(4-cyano-phenyl)-[1,2,4]triazol-4-yl-amino]-propylsulfanyl}-phenyl Ester

HRID 19904
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인쇄 미리보기

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HRID 19904 반응식
[S:1](Cl)(=[O:4])(=[O:3])[NH2:2].C1(C)C=CC=CC=1.[OH:13][C:14]1[CH:19]=[CH:18][C:17]([S:20][CH2:21][CH2:22][CH2:23][N:24]([N:33]2[CH:37]=[N:36][N:35]=[CH:34]2)[C:25]2[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[CH:27][CH:26]=2)=[CH:16][CH:15]=1>O.C(OCC)(=O)C.CN(C)C(=O)C>[C:29]([C:28]1[CH:31]=[CH:32][C:25]([N:24]([N:33]2[CH:37]=[N:36][N:35]=[CH:34]2)[CH2:23][CH2:22][CH2:21][S:20][C:17]2[CH:18]=[CH:19][C:14]([O:13][S:1](=[O:4])(=[O:3])[NH2:2])=[CH:15][CH:16]=2)=[CH:26][CH:27]=1)#[N:30]
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참가 물질

7

반응물 3

HCID 1140TolueneHCID 24499Chlorosulfamic acidHCID 219768664-{[3-(4-Hydroxy-phenylsulfanyl)-propyl]-[1,2,4]triazol-4-yl-amino}-benzonitrile

생성물 1

HCID 21044501Sulfamic Acid 4-{3-[(4-cyano-phenyl)-[1,2,4]triazol-4-yl-amino]-propylsulfanyl}-phenyl Ester

시약·촉매·용매 3

HCID 962Water용매2회
HCID 8857
Ethyl Acetate
용매
HCID 31374Dimethylacetamide용매

실험 절차

Sulphamoyl chloride solution in toluene (3 mL, 0.7 M, 2.1 mmol) was concentrated under reduced pressure (30° C. water bath temperature) to ca. 0.5 mL volume. The residue was cooled to 0° C. (ice bath) and N,N-dimethylacetamide (5 mL) was added. 4-{[3-(4-hydroxy-phenylsulfanyl)-propyl]-[1,2,4]triazol-4-yl-amino}-benzonitrile (CAB02182, 140 mg, 0.40 mmol) was added to the colourless solution and the mixture was stirred for 18 hours at room temperature. Ethyl acetate (50 mL) and water (50 mL) were added to the solution, the organic layer was separated, washed with water (2×30 mL) and brine (20 mL), dried over sodium sulphate and concentrated under reduced pressure. The residue was dissolved in a small amount of acetone and precipitated by addition of hexane. The precipitate was filtered off and dried under high vacuum. Yield: 139 mg (81%) light yellow powder. 1H-NMR (400 MHz, d6-DMSO)=1.74 (tt, J=7.0, 7.0 Hz, 2H), 3.97 (t, J=7.0 Hz, 2H), 6.62 (d, J=9.0 Hz, 2H), 7.22 (d, J=8.6 Hz, 2H), 7.43 (d, J=8.6 Hz, 2H), 7.74 (d, J=9.0 Hz, 2H), 8.03 (s, 2H, —NH2), 9.00 (s, 2H). LRMS (FAB+): 431.1 (100, [M+H]+).

후처리

  1. additionwas added
  2. customthe organic layer was separated
  3. washwashed with water (2×30 mL) and brine (20 mL)
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe residue was dissolved in a small amount of acetone
  7. customprecipitated by addition of hexane
  8. filtrationThe precipitate was filtered off
  9. customdried under high vacuum

출처 및 근거

ORD 기록
ord-67810bad8e98498cb4e734d8a29833e6
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07745472B2

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