Sodium Bicarbonate → 4-Amino-N,N-dimethylbenzamide

HRID 59758Notes

Reaction equation

HRID 59758 reaction equation
[CH3:1][N:2]([CH3:19])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([NH:11]C(=O)OC(C)(C)C)=[CH:7][CH:6]=1)=[O:4].C([O-])(O)=O.[Na+]>CCOC(C)=O.Cl>[NH2:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]([N:2]([CH3:19])[CH3:1])=[O:4])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 24689134Tert-butyl 4-(dimethylcarbamoyl)phenylcarbamate

Product 1

HCID 2355274-Amino-N,N-dimethylbenzamide

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of tert-butyl 4-(dimethylcarbamoyl)phenylcarbamate (Int. 73) (1.11 g, 4.21 mmol) in AcOEt (20 ml), HCl 4M in AcOEt (18 ml, 76 mmol) was added, and the mixture stirred for 5 hours at RT. The pH was adjusted at 6/7 by adding NaHCO3 sat. sol. and aqueous phase was extracted with AcOEt (×3). Organic phase was dried over Na2SO4 and evaporated under reduced pressure to give mg 615 of the title product (Int. 74).

Workup

  1. extractionwas extracted with AcOEt (×3)
  2. dry with materialOrganic phase was dried over Na2SO4
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-1891fcafbcfe45ee8142b0e371867a20
Source dataset
uspto-grants-2016_09
Patent number
US09440954B2

Reaction notes

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