1,3-Dichloro-2-isocyanatobenzene → 1-(2,6-Dichlorophenyl)3-(thieno[3,2-d]pyrimidin-4-yl)urea

HRID 1782069

Reaction equation

HRID 1782069 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]=[C:10]=[O:11].[NH2:12][C:13]1[C:14]2[S:21][CH:20]=[CH:19][C:15]=2[N:16]=[CH:17][N:18]=1>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10]([NH:12][C:13]1[C:14]2[S:21][CH:20]=[CH:19][C:15]=2[N:16]=[CH:17][N:18]=1)=[O:11]

Participants

4

Reactant 2

HCID 6045371,3-Dichloro-2-isocyanatobenzeneHCID 11506485Thieno(3,2-d)pyrimidin-4-amine

Product 1

HCID 99239551-(2,6-Dichlorophenyl)3-(thieno[3,2-d]pyrimidin-4-yl)ureaYield 229.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2,6-Dichlorophenyl isocyanate (0.075 g) was added to a mixture of 4-aminothieno[3,2-d]pyrimidine (Tetrahedron, 1971, 27, 487; 0.201 g) and acetonitrile (16 ml) and the resultant mixture was stirred at ambient temperature for 16 hours. The precipitate was isolated and washed in turn with diethyl ether and methanol. There was thus obtained the title compound (0.31 g); NMR Spectrum: (DMSOd6) 7.25 (t, 1H), 7.45 (d, 1H), 7.55 (d, 1H), 7.95 (d, 1H), 8.4 (s, 1H), 8.8 (s, 1H), 11.7 (br s, 1H); Mass Spectrum: M+H+ 339 and 341; Elemental Analysis: Found C, 45.8; H 2.4; N, 16.5; C13H8Cl2N4OS requires C, 46.03; H, 2.38; N, 16.52%.

Workup

  1. customThe precipitate was isolated
  2. washwashed in turn with diethyl ether and methanol

Sources & evidence

ORD record
ord-8db3ef97975143c1821bcb5b829ec461
Source dataset
uspto-grants-2009_03
Patent number
US07498335B2

Linked notes

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