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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Hydrochloric Acid → HCID 178433880, 화합물

HRID 910335
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HRID 910335 반응식
[NH2:1][C:2]1[C:3]([OH:17])=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([OH:16])=[O:15])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.Cl.N([O-])=O.[Na+].S(=O)(=O)(O)[NH2:24].[CH3:28][C:29]1[CH:30]=[C:31]([N:36]2[C:40]([OH:41])=[CH:39][C:38]([CH3:42])=[N:37]2)[CH:32]=[CH:33][C:34]=1[CH3:35]>O.C(N(CC)CC)C.CO>[CH3:35][C:34]1[CH:33]=[CH:32][C:31]([N:36]2[N:37]=[C:38]([CH3:42])/[C:39](=[N:24]/[NH:1][C:2]3[CH:7]=[CH:6][CH:5]=[C:4]([C:8]4[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([OH:16])=[O:15])[CH:9]=4)[C:3]=3[OH:17])/[C:40]2=[O:41])=[CH:30][C:29]=1[CH3:28]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 5

HCID 313Hydrochloric Acid2회HCID 5987Sulfamic AcidHCID 114923323-(3-Amino-2-hydroxyphenyl)benzoic acidHCID 23668193Sodium NitriteHCID 178429255HCID 178429255, 화합물

생성물 1

HCID 178433880HCID 178433880, 화합물

시약·촉매·용매 3

HCID 887
Methanol
용매
HCID 962Water용매2회
HCID 8471Triethylamine용매

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온도
22 °C

실험 절차

Crystalline 3′-amino-2′-hydroxybiphenyl-3-carboxylic acid form II (50 g, 218 mmol, PXRD pattern at FIG. 34) (Supplier: Topharman Shangai Co., Ltd; Batch No: BPCA: 090921BPCA) was added to a solvent mixture of methanol (1 L) and hydrochloric acid, 4 M (137 mL) in a 1 L reactor with stirring at room temperature (cca 22° C.). The resulting solution was stirred for ½ h and then cooled to 0-5° C. A refrigerated solution of sodium nitrite (15 g, 217 mmol) in water (50 mL) was added to the reaction mixture over 20 min (maintaining the reaction temperature below 10° C.) and the stirring was continued for 1 h. A Solution of sulfamic acid (2.22 g, 23 mmol) in water (50 mL) was added to the reaction mixture and stirred for 1 h at 5° C. The resulting reaction mixture was heated to room temperature and triethylamine (cca 80 mL) was added to adjust to pH 7-8. Crystalline 1-(3,4-dimethylphenyl)-3-methyl-1H-pyrazol-5-ol (“pyrazole”) form II (44 g, 218 mmol, PXRD pattern at FIG. 33) (Supplier: Topharman Shangai Co., Ltd; Batch No: 090805PYRAZOL) was added in one portion to the reaction mixture and stirred for 2 h at room temperature, maintaining the pH 7-8. Hydrochloric acid (4 M, cca 40 mL) was added to adjust the pH to 1.8 over 20 minutes with stirring. The precipitated solid was filtered, washed with mixture of MeOH:water (1:1, 60 mL) and dried at 40° C./5 bar for about 18 h to yield 100 g (90%) of EBP as a bright orange powder. PXRD analysis provided the diffractogram as shown in FIG. 20. DSC analysis provided the thermogram as shown in FIG. 21

후처리

  1. stirringThe resulting solution was stirred for ½ h
  2. temperaturecooled to 0-5° C
  3. temperaturemaintaining the reaction temperature below 10° C.) and the stirring
  4. stirringstirred for 1 h at 5° C
  5. customThe resulting reaction mixture
  6. temperaturewas heated to room temperature
  7. stirringstirred for 2 h at room temperature
  8. temperaturemaintaining the pH 7-8
  9. customover 20 minutes
  10. stirringwith stirring
  11. filtrationThe precipitated solid was filtered
  12. washwashed with mixture of MeOH:water (1:1, 60 mL)
  13. customdried at 40° C./5 bar for about 18 h
  14. customto yield 100 g (90%) of EBP as a bright orange powder
  15. customPXRD analysis provided the diffractogram
  16. customDSC analysis provided the thermogram

출처 및 근거

ORD 기록
ord-b6dd9fd70cc04ec495c81b49ece6068d
출처 데이터셋
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08022093B2

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