Water → N-(3-Carbomethoxy-5-methyl-2-thienyl)-2-methylpropanamide

HRID 1448708Notes

Reaction equation

HRID 1448708 reaction equation
[C:1](Cl)(=[O:5])[CH:2]([CH3:4])[CH3:3].[CH3:7][O:8][C:9]([C:11]1[CH:15]=[C:14]([CH3:16])[S:13][C:12]=1[NH2:17])=[O:10].O>CN(C)P(N(C)C)(N(C)C)=O>[C:9]([C:11]1[CH:15]=[C:14]([CH3:16])[S:13][C:12]=1[NH:17][C:1](=[O:5])[CH:2]([CH3:4])[CH3:3])([O:8][CH3:7])=[O:10]

Participants

5

Reactant 3

HCID 962WaterHCID 62325Isobutyryl chlorideHCID 675878Methyl-2-amino-5-methyl-3-thiophenecarboxylate

Product 1

HCID 23341602N-(3-Carbomethoxy-5-methyl-2-thienyl)-2-methylpropanamideYield 88%

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

isoButyryl chloride (22.4 g) was added dropwise during 40 minutes to a stirred solution of methyl-2-amino-5-methyl-3-thiophenecarboxylate (34.2 g, 0.2 mol) in dry hexamethylphosphoramide (100 ml) kept at 5°-10° C. This temperature was maintained for a further 1 hour and then the reaction was kept at room temperature for 16 hours. The reaction mixture was poured into water (1600 ml) and the yellow precipitate was filtered off, washed with water and dried at 50° C. Recrystallisation of the solid from petroleum ether (b.p. 60°-80° C. yielded cream crystals (39.6 g, 88%), m.p. 63°-65° C.

Workup

  1. customkept at 5°-10° C
  2. temperatureThis temperature was maintained for a further 1 hour
  3. filtrationthe yellow precipitate was filtered off
  4. washwashed with water
  5. customdried at 50° C
  6. customRecrystallisation of the solid from petroleum ether (b.p. 60°-80° C.

Sources & evidence

ORD record
ord-3cbebfc80e164b7d9949587bd96d1718
Source dataset
uspto-grants-1980_02
Patent number
US04187232

Reaction notes

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