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N-cyano-N'-phenylthiourea → HCID 178465973, 화합물

HRID 847181
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HRID 847181 반응식
[C:1]([NH:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=S)#[N:2].C(N=C(NC1C=CC=CC=1)N[C@@H]1C2C=C(C#N)C=CC=2OC(C)(C)[C@H]1O)#N.[C:40]([C:43]1[CH:44]=[CH:45][C:46]2[O:51][C:50]([CH3:53])([CH3:52])[CH:49]([OH:54])[CH:48]([NH2:55])[C:47]=2[CH:56]=1)(=[O:42])[CH3:41].Cl.CN(C)CCCCCN=C=N>CN(C)C=O>[C:40]([C:43]1[CH:44]=[CH:45][C:46]2[O:51][C:50]([CH3:53])([CH3:52])[C@@H:49]([OH:54])[C@H:48]([NH:55][C:4]([NH:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)=[N:3][C:1]#[N:2])[C:47]=2[CH:56]=1)(=[O:42])[CH3:41]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 4711553N-cyano-N'-phenylthioureaHCID 156348051-(4-Amino-3-hydroxy-2,2-dimethylchroman-6-yl)ethan-1-oneHCID 574828161-(3-Dimethylaminopropyl)-2-ethylcarbodiimide hydrochlorideHCID 178431174HCID 178431174, 화합물

생성물 1

HCID 178465973HCID 178465973, 화합물

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

실험 절차

The solution of N-cyano-N'-phenylthiourea (0.98 g, 5.5 mmol, compound of Example 3, part A) and 6-acetyl-3,4-dihydro-2,2-dimethyl-3-hydroxy-4-amino-2H-1-benzopyran (1.0 g, 4.25 mmol, prepared according to Evans et al., J. Med. Chem., 1983, 26, 1582 and J. Med. Chem., 1986, 29, 2194) in dimethylformamide (6 ml) under argon was treated with 1-(3-dimethylaminopropyl)-2-ethylcarbodiimide hydrochloride (1.1 g, 5.5 mmol). The reaction was stirred at room temperature for 2 hours and then partitioned between 10% citric acid and ethyl acetate. The aqueous phase was reextracted with ethyl acetate and the combined extracts were washed with water, sodium bicarbonate and brine. After drying over anhydrous magnesium sulfate, the solvent was evaporated and the residue was crystallized from ethyl acetate to yield the title compound (0.43 g), m.p. 182°-184° C.: 1H NMR (DMSO-d6) δ 9.45 (s, 1H), 7.82 (m, 3H), 7.44 (s, 3H), 7.25 (s, 1H), 6.96 (d, J=9.0 Hz, 1H), 6.0 (s, 1H), 5.1 (m, 1H), 4.15 (m, 1H), 3.8 (s, 1H), 2.61 (s, 3H), 1.52 (s, 3H), 1.29 (s, 3H); 13C NMR (CDCl3) δ 196.2, 159.3, 156.6, 137.6, 129.7, 129.1, 128.4, 124.7, 123.5, 123.3, 117.2, 116.6, 80.0, 71.2, 52.3, 26.7, 26.3, 18.6; IR (KBr) 3412.3, 2978.3, 2935.8, 2179.7, 1670.5, 1602.9, 1577.9, 1493.0, 1359.9, 1271.2, 1126.5 cm-1.

후처리

  1. custompartitioned between 10% citric acid and ethyl acetate
  2. washthe combined extracts were washed with water, sodium bicarbonate and brine
  3. dry with materialAfter drying over anhydrous magnesium sulfate
  4. customthe solvent was evaporated
  5. customthe residue was crystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-d943fab05d9340b896c64cd4de716c1f
출처 데이터셋
uspto-grants-1992_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05140031

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