4-Nitrobenzamide → 5,6-Dihydro-6-hydroxy-5,5-dimethyl-7-(4-nitrobenzamido)-7H-thieno[3,2-b]pyran

HRID 257209

反応式

HRID 257209 の反応式
BrC1C(C)(C)OC2C=CSC=2C1O.[N+:14]([C:17]1[CH:25]=[CH:24][C:20]([C:21]([NH2:23])=[O:22])=[CH:19][CH:18]=1)([O-:16])=[O:15].[H-].[Na+].[OH:28][CH:29]1[C:34]([CH3:36])([CH3:35])[O:33][C:32]2[CH:37]=[CH:38][S:39][C:31]=2[CH:30]1N1CCCC1=O.[K+].[Br-]>CN(C)C=O.O>[OH:28][CH:29]1[C:34]([CH3:36])([CH3:35])[O:33][C:32]2[CH:37]=[CH:38][S:39][C:31]=2[CH:30]1[NH:23][C:21](=[O:22])[C:20]1[CH:19]=[CH:18][C:17]([N+:14]([O-:16])=[O:15])=[CH:25][CH:24]=1

参加物

8

反応物 5

HCID 120914-NitrobenzamideHCID 24758Sodium hydrideHCID 253877Potassium BromideHCID 99034645,6-Dihydro-6-hydroxy-5,5-dimethyl-7-(2-oxopyrrolidin-1-yl)-7H-thieno[3,2-b]pyranHCID 149864866-bromo-5,6-dihydro-7-hydroxy-5,5-dimethyl-7H-thieno[3,2-b]pyran

生成物 1

HCID 149864905,6-Dihydro-6-hydroxy-5,5-dimethyl-7-(4-nitrobenzamido)-7H-thieno[3,2-b]pyran

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

6-Bromo-7-hydroxy-5,6-dihydro-5,5-dimethyl-7H-thieno-[3,2-b]-pyran (6.8 g, 25.8 mmol) and 4-nitrobenzamide (10.7 g, 64.5 mmol) were treated with sodium hydride 60% in oil (2.26 g, 56.8 mmol) in N,N-dimethylformamide (110 mL) using the procedure described for the preparation of 5,6-dihydro-6-hydroxy-5,5- dimethyl-7-(2-oxopyrrolidin -1-yl)-7H-thieno[3,2-b]pyran. The reaction mixture was poured into water and extracted into 10% isopropanol in dichloromethane. The solvent was evaporated in vacuo and the residue was purified by medium pressure chromatography using 2% methanol in dichloromethane as the eluant to give the product, 4.5 g (50%), as a pale yellow solid: mp 183°-186° C. dec; IR (KBr): 3398, 1664, 1644 and 1601 cm-1 ; MS: m/z 349 (MH+); 1H NMR (CDCl3): δ1.35 (s, 3H), 1.50 (s, 3 H), 3.79 (d, J=7.9 Hz, 1H), 4.26 (bs, 1H, exchanges with D2O), 5.19 (d, d, J=7.9 Hz, and J=7.0 Hz, 1H), 6.59 (bd, J=7.0 Hz, 1H, shifts to 6.66 with D2O), 6.63 (d, J=5.4 Hz, 1H), 7.18 (d, J=5.4 Hz, 1H), 7.97 (d, J=8.8 Hz, 2H) and 8.32 (d, J=8.8 Hz, 2H).

後処理

  1. extractionextracted into 10% isopropanol in dichloromethane
  2. customThe solvent was evaporated in vacuo
  3. customthe residue was purified by medium pressure chromatography
  4. customto give the product, 4.5 g (50%)

出典と根拠

ORDレコード
ord-168c82ff6d6f4311b9f556873feb1744
出典データセット
uspto-grants-1993_11
特許番号
US05260453

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