Water → HCID 86720047, compound

HRID 510057Notes

Reaction equation

[F:1][C:2]1[CH:27]=[CH:26][CH:25]=[CH:24][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C:7]([C:14]2[N:19]=[C:18](O)[C:17]([N+:21]([O-:23])=[O:22])=[CH:16][N:15]=2)=[N:6]1.P(Cl)(Cl)([Cl:30])=O.O.C(=O)([O-])O.[Na+]>S1(CCCC1)(=O)=O>[Cl:30][C:18]1[C:17]([N+:21]([O-:23])=[O:22])=[CH:16][N:15]=[C:14]([C:7]2[C:8]3[C:9](=[N:10][CH:11]=[CH:12][CH:13]=3)[N:5]([CH2:4][C:3]3[CH:24]=[CH:25][CH:26]=[CH:27][C:2]=3[F:1])[N:6]=2)[N:19]=1

Participants

Conditions

Temperature: 120 °C

Procedure

109.00 g (249.95 mmol) of the compound from example 78A were initially charged in sulfolane (490 ml), then 55.92 ml (599.88 mmol) of phosphoryl chloride were added and the mixture was heated to 120° C. for 1 h. After cooling, the mixture was added cautiously to water (3 l) and stirred for 15 min. Sodium hydrogencarbonate was added in portions until the pH was 6. The precipitate formed was filtered off with suction and washed with water. The residue was stirred with 200 ml of dichloromethane/methanol (v/v=4:1) for 30 min, filtered off with suction, washed with dichloromethane, acetone and petroleum ether and dried under high vacuum. This gave 63.00 g (62% of theory) of the title compound.

Workup

temperatureAfter cooling
customThe precipitate formed
filtrationwas filtered off with suction
washwashed with water
stirringThe residue was stirred with 200 ml of dichloromethane/methanol (v/v=4:1) for 30 min
filtrationfiltered off with suction
washwashed with dichloromethane, acetone and petroleum ether
customdried under high vacuum

Sources & evidence

ORD record: ord-b1bf6865c1264478b7b0bd0caf81a5f5
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096592B2

Reaction notes

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