Cyanamide → HCID 25140756, 화합물

HRID 1669137노트

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HRID 1669137 반응식
[N+:1]([C:4]1[C:14]([NH2:15])=[CH:13][C:7]2[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:6]=2[CH:5]=1)([O-])=[O:2].[N:16]#[C:17][NH2:18].[CH]Cl.[OH-].[Na+]>O>[N+:1]1([O-:2])[C:4]2[CH:5]=[C:6]3[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C:7]3=[CH:13][C:14]=2[N:15]=[C:17]([NH2:18])[N:16]=1

참가 물질

6

반응물 4

HCID 9864CyanamideHCID 14798Sodium HydroxideHCID 6432229CID 6432229HCID 25140755HCID 25140755, 화합물

생성물 1

HCID 25140756HCID 25140756, 화합물수율 10.3%

시약·촉매·용매 1

HCID 962Water용매

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온도
50 °C

실험 절차

A mixture of nitroaniline 185 (2.26 g, 11.0 mmol) and cyanamide (1.84 g, 43.8 mmol) were mixed together at 100° C., cooled to 50° C., cHCl (10 mL) added carefully and the mixture heated at 100° C. for 4 h. The mixture was cooled to 50° C., 7.5 M NaOH solution added until the mixture was strongly basic and the mixture stirred at 100° C. for 3 h. The mixture was cooled, diluted with water (100 mL), filtered, washed with water (3×20 mL), washed with ether (10 mL) and dried. The residue as purified by chromatography, eluting with 5% MeOH/DCM, to give amine 186 (0.26 g, 10%) as a yellow powder: mp (MeOH) 261-265° C.; 1H NMR [(CD3)2SO] δ 7.86 (s, 1H, H-11), 7.29 (s, 1H, H-5), 7.13 (br s, 2H, NH2), 2.84-2.90 (m, 4H, H-6, H-10), 1.74-1.80 (m, 2H, H-8), 1.58-1.67 (m, 4H, H-7, H-9); 13C NMR [(CD3)2SO] δ 160.2, 152.8, 147.8, 141.2, 127.9, 124.3, 117.8, 35.6, 35.1, 31.3, 29.3, 28.0. Anal. calcd for C12H14N4O: C, 62.6; H, 6.1; N, 24.3. Found: C, 62.9; H, 6.2; N, 24.6%.

후처리

  1. additionwere mixed together at 100° C.
  2. temperaturethe mixture heated at 100° C. for 4 h
  3. temperatureThe mixture was cooled to 50° C.
  4. temperatureThe mixture was cooled
  5. filtrationfiltered
  6. washwashed with water (3×20 mL)
  7. washwashed with ether (10 mL)
  8. customdried
  9. customThe residue as purified by chromatography
  10. washeluting with 5% MeOH/DCM

출처 및 근거

ORD 기록
ord-739730e0226c47deaaabe9bdd12404eb
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07989451B2

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