Dimethylamine → Tert-butyl 4-(dimethylcarbamoyl)phenylcarbamate

HRID 59757Notes

Reaction equation

HRID 59757 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:17]=[CH:16][C:12]([C:13](O)=[O:14])=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:18][N:19](C=O)[CH3:20].CNC.C1COCC1>>[CH3:18][N:19]([CH3:20])[C:13]([C:12]1[CH:16]=[CH:17][C:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:10][CH:11]=1)=[O:14]

Participants

5

Reactant 4

HCID 674DimethylamineHCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 27559314-{[(Tert-butoxy)carbonyl]amino}benzoic acid

Product 1

HCID 24689134Tert-butyl 4-(dimethylcarbamoyl)phenylcarbamate

Procedure

To a solution of 4-(tert-butoxycarbonylamino)benzoic acid (1 g, 4.21 mmol) in DMF (10 ml) CDI (1.025 g, 6.32 mmol) was added. The mixture was stirred at RT for 2 hours. Dimethylamine 2M in THF (3.16 ml, 6.32 mmol) was added, and the mixture stirred at RT for 3 hours. The mixture was poured onto water and extracted with AcOEt (2×). Organic phase was dried over Na2SO4 and evaporated under vacuum to give g 1.25 of Int. 73 which crystallizes on standing.

Workup

  1. stirringthe mixture stirred at RT for 3 hours
  2. additionThe mixture was poured onto water
  3. extractionextracted with AcOEt (2×)
  4. dry with materialOrganic phase was dried over Na2SO4
  5. customevaporated under vacuum
  6. customto give
  7. custom73 which crystallizes

Sources & evidence

ORD record
ord-a151409129904a0d9166afad69f9ac0b
Source dataset
uspto-grants-2016_09
Patent number
US09440954B2

Reaction notes

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