4-Chlorophenyl Isocyanate → HCID 59569062, compound

HRID 1517186Notes

Reaction equation

HRID 1517186 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[N:10]=[C:9]([C:11]2[CH:25]=[CH:24][C:14]3[N:15]([CH3:23])[C:16]([C:18]4[O:19][CH:20]=[CH:21][CH:22]=4)=[N:17][C:13]=3[CH:12]=2)[CH2:8][S:7][C:6]1=[O:26].[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([N:34]=[C:35]=[O:36])=[CH:30][CH:29]=1.C1COCC1>C(N(CC)CC)C>[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([NH:34][C:35]([NH:1][CH2:2][CH2:3][CH2:4][N:5]2[N:10]=[C:9]([C:11]3[CH:25]=[CH:24][C:14]4[N:15]([CH3:23])[C:16]([C:18]5[O:19][CH:20]=[CH:21][CH:22]=5)=[N:17][C:13]=4[CH:12]=3)[CH2:8][S:7][C:6]2=[O:26])=[O:36])=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 76934-Chlorophenyl IsocyanateHCID 8028TetrahydrofuranHCID 59569006HCID 59569006, compound

Product 1

HCID 59569062HCID 59569062, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

120 mg (0.30 mM) of 3-(3-aminopropyl)-5-[2-(2-furyl)-1-methyl-1H-benzimidazol-5-yl]-3,6-dihydro-2H-1,3,4-thiadiazin-2-one and 50.1 mg (0.33 mM) of 1-chloro-4-isocyanatobenzene are added to 2 ml of THF and 164.33 μl (1.33 mM) of triethylamine. The mixture is stirred at room temperature for 20 hours. The solid is filtered off and washed with water and then with isopropanol to give, after drying, 106 mg of N-(4-chlorophenyl)-N′-{3-[5-[2-(2-furyl)-1-methyl-1H-benzimidazol-5-yl]-2-oxo-2H-1,3,4-thiadiazin-3(6H)-yl]propyl}urea.

Workup

  1. filtrationThe solid is filtered off
  2. washwashed with water
  3. customwith isopropanol to give
  4. customafter drying

Sources & evidence

ORD record
ord-f24b1d4da7c0489d92f9b5a6bad28b3a
Source dataset
uspto-grants-2012_07
Patent number
US08232272B2

Reaction notes

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