Tetrahydrofuran → 7-Bromo-6-iodo-8-methoxy-5-methyl-1H-benzo[d][1,3]oxazine-2,4-dione

HRID 17291Notes

Reaction equation

HRID 17291 reaction equation
[NH2:1][C:2]1[C:10]([O:11][CH3:12])=[C:9]([Br:13])[C:8]([I:14])=[C:7]([CH3:15])[C:3]=1[C:4]([OH:6])=[O:5].[O:16]1CCC[CH2:17]1>>[Br:13][C:9]1[C:8]([I:14])=[C:7]([CH3:15])[C:3]2[C:4](=[O:6])[O:5][C:17](=[O:16])[NH:1][C:2]=2[C:10]=1[O:11][CH3:12]

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 860974752-Amino-4-bromo-5-iodo-3-methoxy-6-methylbenzoic Acid

Product 1

HCID 866308077-Bromo-6-iodo-8-methoxy-5-methyl-1H-benzo[d][1,3]oxazine-2,4-dione

Conditions

Temperature
40 °C

Procedure

According to the same method as in Reference Example 31, 2-amino-4-bromo-5-iodo-3-methoxy-6-methylbenzoic acid (I-4) (3.42 g, 8.86 mmol) and bis(trichloromethyl) carbamate (893 mg, 3.01 mmol) were dissolved in dewatered tetrahydrofuran (70 ml) under nitrogen atmosphere, followed by stirring at 40° C. for 1 hour. The reaction liquid was concentrated under reduced pressure to obtain the entitled compound (3.89 g, quant.) as a pale brown solid. Not further purified, this was used in the next reaction.

Workup

  1. customThe reaction liquid
  2. concentrationwas concentrated under reduced pressure
  3. customto obtain the entitled compound (3.89 g, quant.) as a pale brown solid
  4. customNot further purified
  5. customthis was used in the next reaction

Sources & evidence

ORD record
ord-e6864ecd40904878b728d64c6b38f328
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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