Bromhydrol → HCID 11555271, compound

HRID 2301554Notes

Reaction equation

HRID 2301554 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([S:19]([N:22]([CH2:27][CH2:28][O:29]C)[CH2:23][CH2:24][O:25]C)(=[O:21])=[O:20])[C:13]=1[OH:31])=[O:10].[Br-].[Al+3].[Br-].[Br-]>>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([S:19]([N:22]([CH2:23][CH2:24][OH:25])[CH2:27][CH2:28][OH:29])(=[O:21])=[O:20])[C:13]=1[OH:31])=[O:10]

Participants

3

Reactant 2

HCID 166749BromhydrolHCID 11599088HCID 11599088, compound

Product 1

HCID 11555271HCID 11555271, compoundYield 44%

Procedure

A solution of N-(2-bromophenyl)-N′[4-chloro-3-[N″,N″-di-(2-methoxyethyl)-aminosulfonyl]-2-hydroxyphenyl] urea (9.9 mg, 0.018 mmol) and aluminum bromide (4.2 mg, 0.018 mmol) in 2 mL of ethanethio was stirred for 16 hours at room temperature. The mixture was concentrated. The residue was diluted with ethyl acetate, then washed with 1 N aq. HCl, the organic layer was dried over MgSO4 and concentrated. Recrystallization from acetone and methanol gave the desired product (4 mg, 44%). 1H NMR (MeOD-d4): δ 8.30 (d, 1H), 7.92 (d 1H), 7.59 (d, 1H), 7.33 (t, 1H), 7.07 (d, 1H), 7.01 (t, 1H), 3.68 (t, 414), 3.51 (m, 4H).

Workup

  1. concentrationThe mixture was concentrated
  2. additionThe residue was diluted with ethyl acetate
  3. washwashed with 1 N aq. HCl
  4. dry with materialthe organic layer was dried over MgSO4
  5. concentrationconcentrated
  6. customRecrystallization from acetone and methanol

Sources & evidence

ORD record
ord-df542255c1df447fbc63df0aa175c1fc
Source dataset
uspto-grants-2002_12
Patent number
US06500863B1

Reaction notes

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