Dimethylformamide dimethyl acetal → (E)-methyl 4-(benzyloxy)-2-((dimethylamino)methyleneamino)-5-methoxybenzoate

HRID 548474Notes

Reaction equation

HRID 548474 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:9]([O:20][CH3:21])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].CO[CH:24](OC)[N:25]([CH3:27])[CH3:26]>>[CH2:13]([O:12][C:10]1[C:9]([O:20][CH3:21])=[CH:8][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([N:1]=[CH:24][N:25]([CH3:27])[CH3:26])[CH:11]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 11098159Methyl 2-amino-4-(benzyloxy)-5-methoxybenzoate

Product 1

HCID 21697307(E)-methyl 4-(benzyloxy)-2-((dimethylamino)methyleneamino)-5-methoxybenzoate

Conditions

Temperature
100 °C

Procedure

A stirred mixture of 70.0 g (244 mmol) of methyl 2-amino-4-benzyloxy-5-methoxybenzoate (Phytochemistry 1976, 15, 1095) and 52 ml of dimethylformamide dimethyl acetal was heated at 100° C. for 1.5 h, cooled, and evaporated directly under high vacuum to give 81.3 g of off-white solid, mp 134-140° C.; NMR (CDCl3) d 3.01 (s, Me2N).

Workup

  1. temperaturecooled
  2. customevaporated directly under high vacuum

Sources & evidence

ORD record
ord-e6f1b38c981e4d4c90e508162ded3eb8
Source dataset
uspto-grants-2011_05
Patent number
USRE042376E1

Reaction notes

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