Hydrochloric Acid → 2-amino-4-oxo-7-(thiophen-3-ylmethyl)-3,5-dihydropyrrolo[3,2-d]pyrimidine-6-diazonium;chloride

HRID 1770314Notes

Reaction equation

[ClH:1].[NH2:2][C:3]1[NH:4][C:5](=[O:19])[C:6]2[NH:11][C:10]([NH2:12])=[C:9]([CH2:13][C:14]3[CH:18]=[CH:17][S:16][CH:15]=3)[C:7]=2[N:8]=1.Cl.[N:21]([O-])=O.[Na+]>O>[Cl-:1].[NH2:2][C:3]1[NH:4][C:5](=[O:19])[C:6]2[NH:11][C:10]([N+:12]#[N:21])=[C:9]([CH2:13][C:14]3[CH:18]=[CH:17][S:16][CH:15]=3)[C:7]=2[N:8]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Charged 23.4 kg (74.1 mol) of 2,6-diamino-3,5-dihydro-7-(3-thienylmethyl)-4H-pyrrolo[3,2-d]pyrimidin-4-one, hydrochloride, monohydrate (U.S. Pat. No. 4,923,872), 240 L water and 14.9 kg (147.1 mol) 36% hydrochloric acid to a nitrogen-purged 800 L reactor. The resulting slurry is cooled to 0° C. A solution of 7.9 kg (114.5 mol) sodium nitrite in 20 L water is added to the slurry over 40 minutes. The reaction mixture is heated to 20° C. and held at that temperature for 1.3 hours. The product is collected and washed with 90 n water yielding 63.5 kg of the title compound as a water wet cake.

Workup

temperatureThe reaction mixture is heated to 20° C.
customThe product is collected
washwashed with 90 n water yielding 63.5 kg of the title compound as a water wet cake

Sources & evidence

ORD record: ord-ccb2a59bcbfc4139918376fb8980d855
Source dataset: uspto-grants-1995_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05386031

Reaction notes

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