Hydrogen Bromide → HCID 86758328, compound

HRID 2228438Notes

Reaction equation

HRID 2228438 reaction equation
OC[C:3]1C(=O)N(NC2C=CC=CC=2)C(=O)[NH:7][CH:8]=1.Br.BrC[C:21]1[CH:22]=[C:23]([CH:33]=[CH:34][CH:35]=1)[NH:24][C:25]1[NH:30][C:29](=[O:31])[NH:28][C:27](=[O:32])[CH:26]=1.C([S-:38])#N.[K+]>C(O)(=O)C>[SH:38][C:21]1[CH:22]=[C:23]([CH:33]=[CH:34][CH:35]=1)[N:24]([CH2:3][C:8]#[N:7])[C:25]1[NH:30][C:29](=[O:31])[NH:28][C:27](=[O:32])[CH:26]=1

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 516872Potassium thiocyanateHCID 18469913HCID 18469913, compound2×HCID 86758329HCID 86758329, compound

Product 1

HCID 86758328HCID 86758328, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

6-chlorouracil (1 mmol) and meta-aminobenzyl alcohol (2.0 mmol) were dissolved in 10 ml 2-methoxyethanol to form a reaction mixture. The mixture was then stirred at reflux for 10 hours to form 6-(meta-hydroxymethyl anilino)uracil with a yield of 86%. The hydroxy group was displaced by a bromo group by reacting the hydroxymethyl anilino-uracil (0.5 mmol) with 30% HBr in acetic acid (10 ml), thus forming 6-(meta-bromomethyl anilino)uracil with a yield of 90%. The bromo group was further replaced by a thiocyanate group by reacting 0.4 mmol 6-(meta-bromomethyl anilino)uracil with 2 mmol KSCN to form 6-(meta-mercaptocyanomethyl anilino)uracil (MMCMAU) with a yield of 80%. mMCMAU was then hydrolyzed to 6-(meta-thiomethyl anilino)uracil in 5 mL of 2N NaOH. The final product, 6-(meta-disulfidemethyl anilino)uracil, was formed quantitatively by reacting 6-(meta-thiomethyl anilino)uracil with methyl methane thiosulfonate in 2 molar excess.

Sources & evidence

ORD record
ord-a5177e3702c24fc7af479d0c4749cc3b
Source dataset
uspto-grants-2002_07
Patent number
US06417180B1

Reaction notes

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