4-Methylphenyl isocyanate → HCID 71621787, compound

HRID 871018Notes

Reaction equation

HRID 871018 reaction equation
[NH2:1][C:2]1[S:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=2)[C:3]=1[C:14]([NH2:16])=[O:15].C(N(CC)C(C)C)(C)C.[C:26]1([CH3:35])[CH:31]=[CH:30][C:29]([N:32]=[C:33]=[O:34])=[CH:28][CH:27]=1>C(Cl)Cl>[NH2:1][C:2]1[S:6][N:5]=[C:4]([C:7]2[CH:8]=[CH:9][C:10]([NH:13][C:33]([NH:32][C:29]3[CH:30]=[CH:31][C:26]([CH3:35])=[CH:27][CH:28]=3)=[O:34])=[CH:11][CH:12]=2)[C:3]=1[C:14]([NH2:16])=[O:15]

Participants

5

Reactant 3

HCID 693254-Methylphenyl isocyanate2×HCID 81531DiisopropylethylamineHCID 71621924HCID 71621924, compound

Product 1

HCID 71621787HCID 71621787, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-amino-3-(4-aminophenyl)isothiazole-4-carboxamide (25 mg, 0.11 mmol), N,N-diisopropylethylamine (0.047 mL, 0.27 mmol), and para-tolyl isocyanate (0.016 mL, 0.13 mmol) in 0.9 mL DCM was reacted at room temperature. After 1 hour an additional 0.006 mL para-tolyl isocyanate was added, and then 0.004 mL at 3.5 hrs. At 21 hours the reaction was quenched with 1 mL MeOH, stirred 10 min at rt, and then evaporated. The residue was triturated with EtOAc which afforded the title compound as a pale yellow solid (28 mg, 72%).

Workup

  1. customwas reacted at room temperature
  2. customAt 21 hours the reaction was quenched with 1 mL MeOH
  3. customevaporated
  4. customThe residue was triturated with EtOAc which

Sources & evidence

ORD record
ord-46b4d4b01c864ea1bc3e30ae6d9f2feb
Source dataset
uspto-grants-2015_03
Patent number
US08969583B2

Reaction notes

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