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Dimethyl Sulfoxide → N-(5,7-dimethoxy[1,2,4]triazolo-[1,5-a]pyrimidin-2-yl)-2,6-dichlorobenzene-sulfonamide

HRID 411112
Notes
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Reaction equation

HRID 411112 reaction equation
[NH2:1][C:2]1[N:14]=[C:5]2[N:6]=[C:7]([O:12][CH3:13])[CH:8]=[C:9]([O:10][CH3:11])[N:4]2[N:3]=1.[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[C:17]=1[S:23](Cl)(=[O:25])=[O:24].N1C=CC=CC=1.CS(C)=O>C(#N)C>[CH3:13][O:12][C:7]1[CH:8]=[C:9]([O:10][CH3:11])[N:4]2[N:3]=[C:2]([NH:1][S:23]([C:17]3[C:18]([Cl:22])=[CH:19][CH:20]=[CH:21][C:16]=3[Cl:15])(=[O:25])=[O:24])[N:14]=[C:5]2[N:6]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 1049PyridineHCID 5221832,6-DichlorobenzenesulfonylchlorideHCID 11194901[1,2,4]Triazolo[1,5-a]pyrimidin-2-amine, 5,7-dimethoxy-

Product 1

HCID 12056874N-(5,7-dimethoxy[1,2,4]triazolo-[1,5-a]pyrimidin-2-yl)-2,6-dichlorobenzene-sulfonamideYield 92%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Amino-5,7-dimethoxy[1,2,4]triazolo[1,5-a]-pyrimidine (0.75 g, 3.8 mmol) and 2,6-dichlorobenzene-sulfonyl chloride (1.86 g, 7.6 mmol) were mixed in dry acetonitrile (15 mL). To this mixture was added dry pyridine (0.61 mL) and dry DMSO (54 μL, 0.7 mmol). The mixture was allowed to stir at room temperature. After 24 hours, the solvent was removed in vacuo, the residue was partitioned between CH2Cl2 (300 mL) and 2N HCl and the solids were collected by vacuum filtration to give a white solid A. The CH2Cl2 was dried (MgSO4) and removed in vacuo to give a white solid B. Both HPLC and NMR indicated that solid A and B are product. The solids were combined to afford the product as a white powder (1.41 g, 92%). mp 211-213° C. Anal: Cacld for C13H11Cl2N5O4S: C, 38.63; H, 2.74; N, 17.33; S, 7.93; found: C, 38.11; H, 2.68; N, 16.83; S, 7.77. 1H NMR (DMSO-d6): δ 12.4 (bs, 1H); 7.64-7.54 (m, 3H); 6.26 (s, 1H); 4.07 (s, 3H); 3.88 (s, 3H).

Workup

  1. customthe solvent was removed in vacuo
  2. customthe residue was partitioned between CH2Cl2 (300 mL) and 2N HCl
  3. filtrationthe solids were collected by vacuum filtration
  4. customto give a white solid A
  5. dry with materialThe CH2Cl2 was dried (MgSO4)
  6. customremoved in vacuo
  7. customto give a white solid B

Sources & evidence

ORD record
ord-d29b6c1a44644505b2ad52edf33606bb
Source dataset
uspto-grants-2003_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06559101B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes