Chlorosuccinimide → 3-[3-chloro-4-[(2,4-difluorobenzyl)oxy]-6-methyl-2-oxopyridin-1(2H)-yl]-4-methylbenzoic acid

HRID 1832080ノート

反応式

HRID 1832080 の反応式
[F:1][C:2]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:3]=1[CH2:4][O:5][C:6]1[CH:11]=[C:10]([CH3:12])[N:9]([C:13]2[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=2[CH3:22])[C:16]([OH:18])=[O:17])[C:8](=[O:23])[CH:7]=1.C1C(=O)N([Cl:36])C(=O)C1>ClC(Cl)C(O)=O.ClC(Cl)C>[Cl:36][C:7]1[C:8](=[O:23])[N:9]([C:13]2[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=2[CH3:22])[C:16]([OH:18])=[O:17])[C:10]([CH3:12])=[CH:11][C:6]=1[O:5][CH2:4][C:3]1[CH:24]=[CH:25][C:26]([F:28])=[CH:27][C:2]=1[F:1]

参加物

5

反応物 2

HCID 31398ChlorosuccinimideHCID 220503253-[4-[(2,4-difluorobenzyl)oxy]-6-methyl-2-oxopyridin-1(2H)-yl]-4-methylbenzoic Acid

生成物 1

HCID 220510673-[3-chloro-4-[(2,4-difluorobenzyl)oxy]-6-methyl-2-oxopyridin-1(2H)-yl]-4-methylbenzoic acid収率 52%

試薬・触媒・溶媒 2

HCID 6597Dichloroacetic Acid触媒HCID 63651,1-Dichloroethane溶媒

実験手順

3-[4-[(2,4-Difluorobenzyl)oxy]-6-methyl-2-oxopyridin-1(2H)-yl]-4-methylbenzoic acid (from above) (7.5 g, 19.4 mmol) and NCS (2.6 g, 19.4 mmol) were taken up in 65° C. dichloroethane (100 ml). A catalytic amount of dichloroacetic acid (2 drops) was added. After two hours the solvent was removed in vacuo and the residue was taken up in diethyl ether. The precipitate was collected on a filter pad and then taken up in 50% ethyl acetate/hexanes to remove residual succinimide. The precipitate was collected on a filter pad and then dried in vacuo to produce a white powder (4.2 g, 52%). 1H NMR (300 MHz, CD3OD) δ 8.10 (dd, J=7.85 1.81 Hz, 1H), 7.83 (d, J=8.26, 1.81 Hz, 1H), 7.40 (app q, J=8.26 Hz, 1H), 7.58 (d, J=7.85 Hz, 1H), 7.13-7.06 (m, 2H), 6.74 (s, 1H), 5.40 (s, 2H), 2.14 (s, 3H), 2.04 (s, 3H); ES-MS m/z 420 (M+H). ES-HRMS m/z 420.0786 (M+H calcd for C21H17ClF2NO4 requires 420.0809).

後処理

  1. customwere taken up in 65° C.
  2. customAfter two hours the solvent was removed in vacuo
  3. customThe precipitate was collected on a filter pad
  4. customto remove residual succinimide
  5. customThe precipitate was collected on a filter pad
  6. customdried in vacuo

出典と根拠

ORDレコード
ord-364229657eff43c69947ce6e0ca2a2ad
出典データセット
uspto-grants-2006_06
特許番号
US07067540B2

反応ノート

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