Dimethylamine → 2-(2-Iodo-5-methoxyphenyl)-N,N-dimethylacetamide

HRID 4282

Reaction equation

HRID 4282 reaction equation
C(Cl)(=O)C(Cl)=O.[I:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:9]=1[CH2:16][C:17]([OH:19])=O.[CH3:20][NH:21][CH3:22].C(Cl)Cl>C1(C)C=CC=CC=1.CN(C=O)C>[CH3:20][N:21]([CH3:22])[C:17](=[O:19])[CH2:16][C:9]1[CH:10]=[C:11]([O:14][CH3:15])[CH:12]=[CH:13][C:8]=1[I:7]

Participants

7

Reactant 4

HCID 674DimethylamineHCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 8200712-(2-Iodo-5-methoxyphenyl)acetic acid

Product 1

HCID 140254972-(2-Iodo-5-methoxyphenyl)-N,N-dimethylacetamide

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

A 16.7 g (0.19 mole) sample of oxalyl chloride was added dropwise at 0° C. to a solution of 50.0 g (0.17 mole) of 2-iodo-5-methoxybenzeneacetic acid in 310 ml dry toluene and 31.7 ml of DMF. The mixture was allowed to warm to room temperature and stir for 16 hours. The solution was cooled to 0° C. and dimethylamine gas was admitted until the mixture was strongly basic. The mixture was allowed to warm to room temperature and stir for three hours and methylene chloride was added. The organic layer was washed with water, dilute hydrochloric acid, and sodium hydroxide. The organic layer was dried with MgSO4 and evaporated in vacuo to give 54.2 g of N,N-dimethyl-2-iodo-5-methoxybenzeneacetamide, mp 86°-89° C.

Workup

  1. temperatureThe solution was cooled to 0° C.
  2. temperatureto warm to room temperature
  3. stirringstir for three hours
  4. washThe organic layer was washed with water, dilute hydrochloric acid, and sodium hydroxide
  5. dry with materialThe organic layer was dried with MgSO4
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-376b3b80298747838d4894a89b3c46a4
Source dataset
uspto-grants-1988_02
Patent number
US04725602

Linked notes

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