Ammonia → 2,6-Dibromo-4-(6-bromo-benzo[b]naphtho[2,3-d]thiophen-11-yl)-phenoxyl-acetamide

HRID 1873195ノート

反応式

HRID 1873195 の反応式
[NH3:1].[Br:2][C:3]1[CH:14]=[C:13]([C:15]2[C:24]3[C:25]4[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=4[S:27][C:23]=3[C:22]([Br:32])=[C:21]3[C:16]=2[CH:17]=[CH:18][CH:19]=[CH:20]3)[CH:12]=[C:11]([Br:33])[C:4]=1[O:5][CH2:6][C:7](OC)=[O:8]>CO>[Br:2][C:3]1[CH:14]=[C:13]([C:15]2[C:24]3[C:25]4[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=4[S:27][C:23]=3[C:22]([Br:32])=[C:21]3[C:16]=2[CH:17]=[CH:18][CH:19]=[CH:20]3)[CH:12]=[C:11]([Br:33])[C:4]=1[O:5][CH2:6][C:7]([NH2:1])=[O:8]

参加物

4

反応物 2

HCID 222AmmoniaHCID 10794136[2,6-Dibromo-4-(6-bromo-benzo[b]naphtho[2,3-d]thiophen-11-yl)-phenoxy]-acetic acid, methyl ester

生成物 1

HCID 542714622,6-Dibromo-4-(6-bromo-benzo[b]naphtho[2,3-d]thiophen-11-yl)-phenoxyl-acetamide

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Methanol (10 mL) was purged with ammonia gas for 10 min at 0° C. [2,6-dibromo-4-(6-bromo-benzo[b]naphtho[2,3-d]thiophen-11-yl)-phenoxy]-acetic acid, methyl ester (0.50 g, 0.787 mmol) was added and the vessel was sealed, warmed to room temperature and stirred for two days. The reaction mixture was concentrated, diluted with ether and filtered. The solid was boiled in ethyl acetate (8 mL), hot filtered and washed with ethyl acteate and pentane and dried in vacou to provide the title compound as an off white solid (0.22 g, 45%): mp 263-265° C.: NMR (DMSO-d6); δ8.29 (d, J=8 Hz, 1 H), 8.09 (d, J=8 Hz, 1 H), 7.88 (s, 2 H), 7.80 (ddd, J=8, 7, 1 Hz, 1 H), 7.67-7.51 (m, 5 H), 7.30 (ddd, J=8, 7, 1 Hz, 1 H), 6.71 (d, J=8 Hz, 1H), 4.56 (s, 2 H); MS (EI): [M+], 3 bromine isotope pattern, 617 (30%), 619 (90%) 621 (100%) 623 (40%); Anal. Calc. for C24H14Br3NO2S: C, 46.48, H, 2.28, N, 2.26. Found: C, 45.69, H, 2.02 , N, 2.14.

後処理

  1. additionwas added
  2. customthe vessel was sealed
  3. concentrationThe reaction mixture was concentrated
  4. additiondiluted with ether
  5. filtrationfiltered
  6. filtrationhot filtered
  7. washwashed with ethyl acteate and pentane
  8. customdried in vacou

出典と根拠

ORDレコード
ord-d636e143b98840e7b55965d4def1fa41
出典データセット
uspto-grants-2000_08
特許番号
US06110962

反応ノート

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