Hydrochloric Acid → 2-{2-[N-(2-methyl-2-sulfanylpropyl)carbamoyl]phenyl}benzoic acid

HRID 992590ノート

反応式

HRID 992590 の反応式
Cl.[NH2:2][CH2:3][C:4]([CH3:7])([SH:6])[CH3:5].C(N(CC)CC)C.[CH:15]1[C:25]2[C:24]3[CH:26]=[CH:27][CH:28]=[CH:29][C:23]=3[C:22](=[O:30])[O:21][C:20](=[O:31])[C:19]=2[CH:18]=[CH:17][CH:16]=1.Cl>C(Cl)Cl>[CH3:5][C:4]([SH:6])([CH3:7])[CH2:3][NH:2][C:22]([C:23]1[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=1[C:25]1[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=1[C:20]([OH:31])=[O:21])=[O:30]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 72794Diphenic anhydrideHCID 130491041-Amino-2-methyl-2-propanethiol hydrochloride

生成物 1

HCID 184127982-{2-[N-(2-methyl-2-sulfanylpropyl)carbamoyl]phenyl}benzoic acid収率 99.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To an ice-cooled suspension of 1-amino-2-methyl-2-propanethiol hydrochloride (1.08 g, 7.62 mmol) in methylene chloride (20 mL) was added triethylamine (1.2 mL, 8.61 mmol) followed by dibenzo[c,e]oxepin-5,7-dione (1.68 g, 7.42 mmol). After stirring at room temperature for 1 h, cold 2 N HCl (50 mL) was added. After separation, the aqueous layer was extracted with dichloromethane (2×15 mL). The combined organic layers were washed with brine and dried under sodium sulfate. The solvent was removed and the resulting residue was triturated with hexane to give the title compound as white solid (2.44 g, 98.9%). mp 150-153° C.; 1H NMR (CDCl3, 300 MHz): δ1.03 (s, 3H), 1.12 (s, 3H), 1.36 (s, 1H), 3.15 (dd, J=13.7 and 5.7 Hz, 1H), 3.38 (dd, J=13.7 and 6.9 Hz, 1H), 6.92 (t, J=6.1 Hz, 1H), 7.09-7.17 (m 2H), 7.38-7.48 (m, 4H), 7.57-7.61 (m, 1H), 7.80-7.83 (m, 1H); 13C NMR (CDCl3, 75 MHz,): δ29.36, 29.75, 44.66, 53.01, 127.28, 127.96, 128.04, 129.38, 129.93, 130.06, 130.20, 131.19, 132.02, 134.69, 138.90, 140.11, 170.99, 171.24; LCMS (m/e): 330 (M+1).

後処理

  1. customAfter separation
  2. extractionthe aqueous layer was extracted with dichloromethane (2×15 mL)
  3. washThe combined organic layers were washed with brine
  4. customdried under sodium sulfate
  5. customThe solvent was removed
  6. customthe resulting residue was triturated with hexane

出典と根拠

ORDレコード
ord-31a34c28163c468a9ba5ea74de995ad3
出典データセット
uspto-grants-2002_10
特許番号
US06469065B1

反応ノート

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