2-Chloro-p-toluidine-5-sulfonic acid → HCID 9802203, compound

HRID 2111959Notes

Reaction equation

HRID 2111959 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([CH3:9])=[CH:4][C:3]=1[S:10]([OH:13])(=[O:12])=[O:11].[Br:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([N:21]=[C:22]=[O:23])[CH:16]=1.C(N(CC)CC)C>C1COCC1.C(OCC)(=O)C>[Br:14][C:15]1[CH:16]=[C:17]([NH:21][C:22](=[O:23])[NH:1][C:2]2[CH:7]=[C:6]([Cl:8])[C:5]([CH3:9])=[CH:4][C:3]=2[S:10]([OH:13])(=[O:12])=[O:11])[CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 69352-Chloro-p-toluidine-5-sulfonic acidHCID 8471TriethylamineHCID 1410013-Bromophenyl isocyanate

Product 1

HCID 9802203HCID 9802203, compoundYield 65.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Amino-4-chloro-5-methyl-benzenesulfonic acid (665 mg, 3.0 mmol) was suspended in 30 ml dry THF and 1-bromo-3-isocyanato-benzene (624 mg, 3.15 mmol) was added. Upon addition of triethylamine (354 mg, 3.15 mmol) the suspension cleared and became a solution. The solution was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate (150 ml) and washed with diluted aqueous hydrochloric acid. The organic phase was dried over sodium sulphate and reduced to dryness under vacuum. The title compound was recrystallised from ethyl acetate/heptane to give 820 mg (65%) of white crystals (m.p. 275° C.; decomposition).

Workup

  1. washwashed with diluted aqueous hydrochloric acid
  2. dry with materialThe organic phase was dried over sodium sulphate
  3. customThe title compound was recrystallised from ethyl acetate/heptane

Sources & evidence

ORD record
ord-fbbd4cfa3c334f4e8421d8ebbef0c127
Source dataset
uspto-grants-2009_04
Patent number
US07521480B2

Reaction notes

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