3,4-Diaminotoluene → HCID 87732527, compound

HRID 2377269Notes

Reaction equation

HRID 2377269 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11][N:10]=C1)([N:3]1[CH:7]=[CH:6]N=C1)=[S:2].[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]([C:49]2[CH:54]=[CH:53][C:52]([O:55][CH3:56])=[CH:51][CH:50]=2)[N:22]2[C:26]3[C:27]4[C:32]([CH2:33][C:25]=3[C:24]([C:42]3[S:46]C(CN)=[CH:44][CH:43]=3)=[N:23]2)=[CH:31][C:30]([CH2:34][N:35]2[CH2:40][CH2:39][N:38]([CH3:41])[CH2:37][CH2:36]2)=[CH:29][CH:28]=4)=[CH:17][CH:16]=1.N[C:58]1[CH:59]=[C:60]([CH3:65])[CH:61]=CC=1N>C(#N)C.N1C=CC=CC=1>[NH2:10][C:11]1[CH:58]=[CH:59][C:60]([CH3:65])=[CH:61][C:12]=1[NH:8][C:1]([NH:3][CH2:7][C:6]1[S:46][C:42]([C:24]2[C:25]3[CH2:33][C:32]4[C:27](=[CH:28][CH:29]=[C:30]([CH2:34][N:35]5[CH2:40][CH2:39][N:38]([CH3:41])[CH2:37][CH2:36]5)[CH:31]=4)[C:26]=3[N:22]([CH:21]([C:18]3[CH:19]=[CH:20][C:15]([O:14][CH3:13])=[CH:16][CH:17]=3)[C:49]3[CH:50]=[CH:51][C:52]([O:55][CH3:56])=[CH:53][CH:54]=3)[N:23]=2)=[CH:43][CH:44]=1)=[S:2]

Participants

6

Reactant 3

HCID 103323,4-DiaminotolueneHCID 802641,1'-ThiocarbonyldiimidazoleHCID 69203737HCID 69203737, compound

Product 1

HCID 87732527HCID 87732527, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolvent2×HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 1,1′-thiocarbonyldiimidazole (26 mg, 0.13 mmol) in acetonitrile (1 mL) and pyridine (1 mL) was cooled to about −20 C and a solution of Example 395 (60 mg, 0.09 mmol) in acetonitrile (1 mL) and pyridine (1 mL) was added dropwise. The reaction mixture was stirred for about 2.5 hours while being allowed to warm to room temperature, then 3,4-diaminotoluene (25 mg, 0.2 mmol) was added and the solution was stirred at about 35 C for about 2 days. The mixture was evaporated to dryness and the residue was purified by flash column chromatography on silica gel using dichloromethane/methanol (10:1) as eluent to provide Example 605. MS (ESI): m/z 771 (M+H)+.

Workup

  1. stirringthe solution was stirred at about 35 C for about 2 days
  2. customThe mixture was evaporated to dryness
  3. customthe residue was purified by flash column chromatography on silica gel
  4. customto provide Example 605

Sources & evidence

ORD record
ord-b7b0722cad5447ad969e5765c96e6f8f
Source dataset
uspto-grants-2008_12
Patent number
US07468371B2

Reaction notes

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