Phenyl Isothiocyanate → 1-Phenyl-3-[4-(phenylsulfamoyl)phenyl]thiourea

HRID 889512

반응식

HRID 889512 반응식
C(N(CC)CC)C.[C:8]1([N:14]=[C:15]=[S:16])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[NH2:17][C:18]1[CH:23]=[CH:22][C:21]([S:24]([NH:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)(=[O:26])=[O:25])=[CH:20][CH:19]=1>C1COCC1>[CH:11]1[CH:12]=[CH:13][C:8]([NH:14][C:15]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([S:24]([NH:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)(=[O:26])=[O:25])=[CH:20][CH:19]=2)=[S:16])=[CH:9][CH:10]=1

참가 물질

5

반응물 3

HCID 7673Phenyl IsothiocyanateHCID 8471TriethylamineHCID 31390Sulfabenz

생성물 1

HCID 34210331-Phenyl-3-[4-(phenylsulfamoyl)phenyl]thiourea

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Triethylamine (0.07 mL, 0.5 mmol) and phenyl isothiocyanate (2.1 mL, 11 mmol) were added sequentially to a solution of 4 (2.48 g, 10 mmol) in dry THF (10 mL). After heating under reflux for 48 h, all volatiles were removed under vacuum, and the resulting crude material was purified by flash chromatography on silica gel (hexanes/acetone, 3:1) to afford N-phenyl-4-[[(phenylamino)thioxomethyl]amino]benzenesulfonamide (5, also called LED209) (1.34 g, 35%) as a white solid, mp 160-162° C. 1H NMR (CD3COCD3, 300 MHz) δ 9.35 (br s, 1H), 9.30 (br s, 1H), 8.98 (br s, 1H), 7.80-7.72 (m, 4H), 7.51-7.47 (m, 2H), 7.38-7.33 (m, 2H), 7.28-7.16 (m, 5H), 7.08-7.04 (m, 1H); 13C NMR (CD3COCD3, 75 MHz) δ 180.2, 143.9, 138.9, 138.2, 135.2, 129.3 (2C), 129.1 (2C), 127.9 (2C), 125.8, 124.6 (3C), 122.8 (2C), 120.8 (2C).

후처리

  1. temperatureAfter heating
  2. temperatureunder reflux for 48 h
  3. customall volatiles were removed under vacuum
  4. customthe resulting crude material was purified by flash chromatography on silica gel (hexanes/acetone, 3:1)

출처 및 근거

ORD 기록
ord-38b261d94b1547c787c1712d9d88442a
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08252841B2

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