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

HRID 1873195Notes

Reaction equation

HRID 1873195 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d636e143b98840e7b55965d4def1fa41
Source dataset
uspto-grants-2000_08
Patent number
US06110962

Reaction notes

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