Water → HCID 59405021, compound

HRID 1672185Notes

Reaction equation

HRID 1672185 reaction equation
[O:1]=[C:2]1[NH:8][C:7]2[CH:9]=[C:10]([C:13]([F:16])([F:15])[F:14])[CH:11]=[CH:12][C:6]=2[C:5](=[O:17])[CH:4](C(OC)=O)[CH2:3]1.O>CN1C(=O)CCC1>[F:16][C:13]([F:14])([F:15])[C:10]1[CH:11]=[CH:12][C:6]2[C:5](=[O:17])[CH2:4][CH2:3][C:2](=[O:1])[NH:8][C:7]=2[CH:9]=1

Participants

4

Reactant 2

HCID 962Water2×HCID 59404990HCID 59404990, compound

Product 1

HCID 59405021HCID 59405021, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
135 °C

Procedure

A 22 L reactor was charged with a solution of methyl 2,5-dioxo-8-(trifluoromethyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepine-4-carboxylate [670 g, 2.22 mol] in NMP (4 L, 6 vol). Water (67 mL, 0.1 vol) was added and the resulting solution was slowly heated to 135° C. The reaction was continued for 15 h when HPLC analysis indicated >99% conversion. The reaction was cooled to ambient temperature. Water (8.7 L, 13 vol) was added slowly with vigorous stirring resulting in a suspension. The suspension was stirred at ambient temperature overnight. The solid was collected by filtration and the filter cake was washed with water (1.5 L). The solid was dried to a constant weight in a vacuum oven at 45° C. to obtain 8-(trifluoromethyl)-3,4-dihydro-1H-1-benzazepine-2,5-dione (522 g, 97% recovery) as an off-white solid.

Workup

  1. temperatureThe reaction was cooled to ambient temperature
  2. customresulting in a suspension
  3. stirringThe suspension was stirred at ambient temperature overnight
  4. filtrationThe solid was collected by filtration
  5. washthe filter cake was washed with water (1.5 L)
  6. customThe solid was dried to a constant weight in a vacuum oven at 45° C.

Sources & evidence

ORD record
ord-57def3ac41bf4c80b2b3b61b80064e7f
Source dataset
uspto-grants-2011_08
Patent number
US07998952B2

Reaction notes

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