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

HRID 1873195노트

반응식

HRID 1873195 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d636e143b98840e7b55965d4def1fa41
출처 데이터셋
uspto-grants-2000_08
특허 번호
US06110962

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