Dichloromethane → 4-(1H-indol-3-ylmethyl)-1,3-thiazole

HRID 645945

反応式

HRID 645945 の反応式
C(N)=S.C(Cl)Cl.[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([CH2:16][CH2:17][NH:18][C:19](=S)[SH-:20][CH2:21]C2C=CC=CC=2)=[CH:8]1.CCCCCCS/C(/S)=N\CC1NC2C=CC=CC=2C=1>CC#N.O>[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([CH2:16][C:17]2[N:18]=[CH:19][S:20][CH:21]=2)=[CH:8]1

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 3005587MethanethioamideHCID 178445575HCID 178445575、化合物HCID 178528016HCID 178528016、化合物

生成物 1

HCID 115286104-(1H-indol-3-ylmethyl)-1,3-thiazole収率 71%

試薬・触媒・溶媒 1

HCID 18373917Acetonitrile--water (1/1)溶媒

実験手順

The general method was used with thioformamide to afford a 71% yield (Londergan et al. (1953) J. Am. Chem. Soc., 75:4456-8). 1H NMR (CDCl3) δ 8.76 (d, 1H, SCHN, J=2.0 Hz), 8.11 (br s, 1H, NH), 7.52 (d, 1H, ArH, J=7.6 Hz), 7.36 (d, 1H, ArH, J=8.0 Hz), 7.18 (t, 1H, ArH, J=7.1 Hz), 7.08 (t, 2H, ArH, J=7.4 Hz), 6.90 (s, 1H, ArH), 4.34 (s, 2H, ArCH2). 13C NMR (CDCl3) δ 157.5, 152.5, 122.5, 122.1, 119.4, 119.1, 113.8, 113.5, 111.2, 27.6. IR (CH2Cl2) vmax cm−1: 3626, 3470, 3051, 2987, 1420, 1264. GC: r.t.=15.05 min. EI-MS m/z (%) 214 (100, M+), 213 (86), 186 (15), 154 (14), 130 (51). RP-HPLC (1/1 CH3CN/H2O+0.1% TFA) r.t.=4.408 min.

後処理

  1. customto afford a 71% yield (Londergan et al. (1953) J. Am. Chem. Soc., 75:4456-8)
  2. customr.t.=15.05 min

出典と根拠

ORDレコード
ord-9644528451be4948a15b5140836f23e9
出典データセット
uspto-grants-2010_04
特許番号
US07705022B2

関連ノート

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