1,2-Dichloro-3-isocyanatobenzene → HCID 9886349, compound

HRID 1698914Notes

Reaction equation

HRID 1698914 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]([CH3:10])([CH3:9])[CH3:8])[NH:4][C:3]=1[C:11]([O:13][CH3:14])=[O:12].[Cl:15][C:16]1[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][C:17]=1[N:23]=[C:24]=[O:25]>C(Cl)Cl>[C:11]([C:3]1[NH:4][C:5]([C:7]([CH3:10])([CH3:8])[CH3:9])=[CH:6][C:2]=1[NH:1][C:24]([NH:23][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]([Cl:22])[C:16]=1[Cl:15])=[O:25])([O:13][CH3:14])=[O:12]

Participants

4

Reactant 2

HCID 330501,2-Dichloro-3-isocyanatobenzeneHCID 18322367methyl 3-amino-5-(tert-butyl)-1H-pyrrole-2-carboxylate

Product 1

HCID 9886349HCID 9886349, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of methyl 3-amino-5-tert-butylpyrrole-2-carboxylate (0.99 g, 5.00 mmol) in anh. CH2Cl2 (50 ml) at room temp. was added a solution of 2,3-dichlorophenyl isocyanate (0.948 g, 5.00 mmol) in CH2Cl2 (10 mL) and the resulting mixture was allowed to stir overnight. The resulting white precipitate formed overnight was separated and washed with CH2Cl2 to give the desired urea (1.39 g, 67%) as a white powder: mp 200-201° C.; 1H-NMR (DMSO-d6) δ1.23 (s, 9H), 3.78 (s, 3H), 6.50 (d, J=2.95 Hz, 1H), 7.26-7.30 (m, 2H), 7.88-7.91 (m, 1H), 9.12 (s, 1H), 9.40 (s, 1H), 10.91 (br s, 1H); FAB-LRMS m/z 384 (M+H). Anal. Calcd for C17H19N3O3Cl2: C, 53.14; H, 4.98; N, 10.94. Found: C, 53.03; H, 4.79; N, 10.86.

Workup

  1. customThe resulting white precipitate formed overnight
  2. customwas separated
  3. washwashed with CH2Cl2

Sources & evidence

ORD record
ord-8f30fc242619491891e8259c019bfd99
Source dataset
uspto-grants-2002_02
Patent number
US06344476B1

Reaction notes

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