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

HRID 1803704Notes

Reaction equation

HRID 1803704 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-50cf850e6cb34149aceb08fbb8e83a5d
Source dataset
uspto-grants-2013_01
Patent number
US08349869B2

Reaction notes

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