Sulfanilamide → HCID 10158281, compound

HRID 860761Notes

Reaction equation

HRID 860761 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[C:5]([Cl:17])=[CH:4][N:3]=1.[S:18]([NH2:28])(=[O:27])([C:20]1[CH:25]=[CH:24][C:23]([NH2:26])=[CH:22][CH:21]=1)=[O:19]>CN1C(=O)CCC1>[S:18]([C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:2]2[N:7]=[C:6]([O:8][C:9]3[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=3)[C:5]([Cl:17])=[CH:4][N:3]=2)=[CH:22][CH:21]=1)(=[O:19])(=[O:27])[NH2:28]

Participants

4

Reactant 2

HCID 5333SulfanilamideHCID 58247423HCID 58247423, compound

Product 1

HCID 10158281HCID 10158281, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 2,5 dichloro-4-(4-methoxyphenoxy)pyrimidine (Method 25; 0.65 g, 2.4 mmol) and sulphanilamide (0.38 g, 2.2 mmol) in NMP(1.5 ml) was heated to 100° C. for 4 hours. The reaction mixture was partitioned between water and ethyl acetate. The organic solution was evaporated and the residue purified by column chromatography eluting with 0.1% formic acid, 4% methanol in dichloromethane to afford a solid product (0.17 g, 19%). NMR: 3.81 (s, 3H), 7.05 (d, 2H), 7.10 (s, 2H), 7.22 (d, 2H), 7.50 (d, 4H), 8.50 (s, 1H), 10.6 (br s, 1H); MS [M−H]−: 405, 407.

Workup

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. customThe organic solution was evaporated
  3. customthe residue purified by column chromatography
  4. washeluting with 0.1% formic acid, 4% methanol in dichloromethane

Sources & evidence

ORD record
ord-ffca0da42d7640ccbba6ad4d386710f1
Source dataset
uspto-grants-2006_12
Patent number
US07153964B2

Reaction notes

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