Phosphorus oxychloride → 2-Cyclohexylthiazole-4-carboxylic acid (6-acetyl-3-methoxy-2-methylphenyl)amide

HRID 579655Notes

Reaction equation

HRID 579655 reaction equation
O=P(Cl)(Cl)Cl.[CH:6]1([C:12]2[S:13][CH:14]=[C:15]([C:17]([OH:19])=O)[N:16]=2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.[C:20]([C:23]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([CH3:32])[C:24]=1[NH2:25])(=[O:22])[CH3:21]>N1C=CC=CC=1>[C:20]([C:23]1[C:24]([NH:25][C:17]([C:15]2[N:16]=[C:12]([CH:6]3[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]3)[S:13][CH:14]=2)=[O:19])=[C:26]([CH3:32])[C:27]([O:30][CH3:31])=[CH:28][CH:29]=1)(=[O:22])[CH3:21]

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 234049342-Cyclohexyl-1,3-thiazole-4-carboxylic acidHCID 250673162'-Amino-3'-methyl-4'-methoxyacetophenone

Product 1

HCID 579564522-Cyclohexylthiazole-4-carboxylic acid (6-acetyl-3-methoxy-2-methylphenyl)amideYield 98.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

POCl3 (1.4 mL, 14.9 mmol) was added drop wise at −35° C. over 5 min, to a stirred solution of 2-cyclohexylthiazole-4-carboxylic acid (117, 1.5 g, 7.1 mmol) and 2-acetyl-5-methoxy-6-methylaniline (1.27 g, 7.1 mmol) in dry pyridine (40 mL). After 1 h, the reaction mixture was successively warmed up to room temperature for 2.5 h, evaporated and neutralized with an aqueous solution of sodium bicarbonate. The precipitate was filtered, washed with water and dried to give 2.6 g (95%) of the title compound 118: m/z=373 (M+H)+.

Workup

  1. customevaporated
  2. filtrationThe precipitate was filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-0b83b633f84544878330a100174dbfc4
Source dataset
uspto-grants-2015_05
Patent number
US09040562B2

Reaction notes

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