Pyridine → HCID 70574507, compound

HRID 224492Notes

Reaction equation

HRID 224492 reaction equation
Br.[NH2:2][C:3]1[S:4][CH2:5][C:6](=[CH:8][CH2:9][C:10](=[O:19])[NH:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[N:7]=1.N1C=CC=CC=1.[CH3:26][N:27]=[C:28]=[O:29]>O>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([NH:11][C:10]([CH2:9][CH:8]=[C:6]2[CH2:5][S:4][C:3]([NH:2][C:28]([NH:27][CH3:26])=[O:29])=[N:7]2)=[O:19])=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 1049Pyridine2×HCID 12228Methyl IsocyanateHCID 70574082HCID 70574082, compound

Product 1

HCID 70574507HCID 70574507, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A reaction flask was charged with 3.9 g (0.011 mole) of 2-amino-4-(4-chlorophenylcarbamoylethylidene) thiazole hydrobromide (M.P. 112°-16°; prepared from 4-bromo-4'-chloro-2-methylacetoacetanilide and thiourea in ethanol), 30 ml of pyridine and 1.1 g (0.018 mole) of methyl isocyanate. The solution was allowed to stir overnight at ambient temperature. On the following morning, the pyridine solution was poured into water. The water was decanted from the residual oil. With stirring, the addition of fresh water caused the residue to solidify. The solid was dissolved in hot ethanol. The crystalline material in the cooled mixture was collected on a vacuum filter. There was obtained 1.4 g (38%) of white solid, M.P. 203°-205°. N.M.R. (dimethyl-d6 sulfoxide, CDCl3) ∂1.3-1.6 (CH3, doublet), 2.5-2.8 (NCH3, doublet), 3.5-3.8 (CH), 6.5 (hetero-aromatic), 7.1-7.7 (aromatic), 9.9 and 10.4 [NHC(O)NH].

Workup

  1. customThe water was decanted from the residual oil
  2. stirringWith stirring
  3. additionthe addition of fresh water
  4. dissolutionThe solid was dissolved in hot ethanol
  5. customThe crystalline material in the cooled mixture was collected on a vacuum
  6. filtrationfilter

Sources & evidence

ORD record
ord-b08c628c73cb45d2b11a48b0e57ad09b
Source dataset
uspto-grants-1980_11
Patent number
US04232163

Reaction notes

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