Water → HCID 20183519, compound

HRID 255501Notes

Reaction equation

HRID 255501 reaction equation
[H-].[Na+].[C:3]([C:6]1[CH:11]=[C:10]([C:12](=[O:14])[CH3:13])[C:9]([OH:15])=[CH:8][C:7]=1[NH:16][CH:17]=O)(=[O:5])[CH3:4].C(Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O.[CH3:28]N(C)C=O>>[C:12]([C:10]1[CH:11]=[C:6]2[C:7](=[CH:8][C:9]=1[OH:15])[N:16]([CH2:17][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:28]=[CH:4][C:3]2=[O:5])(=[O:14])[CH3:13]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 20183527HCID 20183527, compound

Product 1

HCID 20183519HCID 20183519, compound

Procedure

A suspension of pre-washed sodium hydride (0.87 g, 0.036 mmol) was stirred at 0° in dry dimethylformamide under nitrogen while N-[2,4-diacetyl-5-hydroxyphenyl]formamide (4.0 g, 18 mmol) was added in small portions. After the addition was complete the mixture was allowed to stir at 0° for 30 minutes, then benzyl bromide (3.lg, 18 mmol) was added all at once. The mixture was stirred for 6 hours during which time the temperature was allowed to rise to 10°. The dark brown solution was poured into a large excess of water, the mixture was acidified to approximately pH 4.0, and was stirred overnight. The off-white solid was filtered off, washed well with water and was dried. The solid was crystallised as white needles 4.8 g (90%) mp 246° -7°.

Workup

  1. additionwas added in small portions
  2. additionAfter the addition
  3. stirringThe mixture was stirred for 6 hours during which time the temperature
  4. customto rise to 10°
  5. stirringwas stirred overnight
  6. filtrationThe off-white solid was filtered off
  7. washwashed well with water
  8. customwas dried
  9. customThe solid was crystallised as white needles 4.8 g (90%) mp 246° -7°

Sources & evidence

ORD record
ord-7bdf21067b6c48d6be6dc1a7aaf980d6
Source dataset
uspto-grants-1987_10
Patent number
US04698345

Reaction notes

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